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Direction of PropagationDirection of PropagationDirection of Propagation45¡LPLEx = RCPLEy = LCPL45¡LPLEx = RCPLEy = LCPL45¡LPLEx = RCPLEy = LCPLCDMQuartz RelaxedQuartzStretchedQuartzCompressedA:B:C: LCPL 
lags behind the RCPL 
by 1/4 !R = + 1/4 !RCPL 
is generated RCPL 
lags behind the LCPL 
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=2(23363%')%'06%6'*:%2&*%'06%:'*:%).%'06%0190%6&6(94%5'2'6%15%2&-<=2(23363%')%'06%6'*:"%%?015%

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Rij ¥ ( µioa ! µjoa ) "ij < 0Positive chiraityof the interactingchromophoresNegative chiraityof the interactingchromophoresRij ¥ ( µioa ! µjoa ) "ij > 0Positive first and negativesecond Cotton effects
Negative first and positivesecond Cotton effects
# (nm)$%+-# (nm)$%+-Positive ECCDNegative ECCDcN"#$%&'!()*85
%%\67&1-)&%).%6V,1')&%,01(231'4%.)(%2%>1&2(4%545'6:"%%?06%,3),8D156%
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,)+&'6(,3),8D156"'"                              (I.6)      
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2&)'06(%EF19+(6%!"#RG"%%X06&%'06%,0():)=0)(65%2(6%2((2&96*%1&%2%,3),8D156%.2501)&%3))81&9%

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2(6%,3)56%1&%5=2,6%2&*%)(16&'6*%1&%2%0631,23%.2501)&"%%?0656%,0():)=0)(65%,2&%>6%1&06(6&'%')%'06%
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5'6(6),06:15'(4%25%
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;1)32V2&'01&%D6(6%50)D&%')%>6%(632'6*%>4%,06:1,23%,)((632-)&%2&*%'06%,)&79+(2-)&%).%
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""''%%!&%#R]cB%!5)6
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"%)&%
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-:6%D1'0%E
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,6&'6(%15%
""'*%%!&%#R]eB%m282&1501B%6'"%23B%,)&'(1>+'6*%>4%'06%U//\%2&234515%).%2>5,151,%2,1*%2&*%2&%
OCOOHOH(S)-(+)-Abscisic AcidOOOHdehydrovomifoliolOOHHOOCOOHOclockwise helicitypositive ECCDc]"#$%&'!()+95
%%?06%U//\%2&234515%).%E
"G<EhG<K>5,151,%2,1*%2&*%*604*();):1.)31)3"%%?06%:)5'%
5'2>36%,)&.)(:2-)&%).%62,0%:)36,+36%15%235)%50)D&"%%?06%*)+>36<062*6*%2(()D5%
1&*1,2'6%'06%*1=)36%:):6&'%).%62,0%,0():)=0)(6%D1'0%'06%>)3*%2(()D%>61&9%1&%.()&'%

2&*%'06%*2506*%2(()D%1&%>2,8"%%?06%,0():)=0)(65%2(6%1&%2%,3),8D156%0631,23%
2((2&96:6&'%'0+5B%2%=)51-;6%U//\%15%6V=6,'6*%2&*%)>56(;6*"
(,2&23)9%).%8&)D&%,)&79+(2-)&B%*604*();):1.
)31)3B%.)(%,):=2(15)&"%%P)'0%2>5,151,%2,1*%2&*%
*604*();):1.)31)3%02;6%1&*6=6&*6&'%+&52'+(2'6*%,2(>)&43%.+&,-)&231-65%2((2&96*%1&%2%
,3),8D156%0631,1'4%*+6%')%'06%04*()V43%,6&'6("
'+&(,%%P61&9%'02'%'06%,)&79+(2-)&%).%
*604*();):1.)31)3%D25%8&)D&B%'06%)>56(;6*%=)51-;6%U//\%,)+=36'%D25%6V=6,'6*"%%K%=)51-;6%

U//\%,)+=36'%D25%235)%)>56(;6*%.)(%2>5,151,%2,1*%'0+5B%U//\%2&234515%,)&7(:6*%'02'%'06%
04*()V43%,)&79+(2-)&%D25%,)((6,'34%32>636*%""OOOOOMeOMeOarnottin IIA = -118
OOOOMeHHMeMeHHOMeOMeMeOOMeOOOOMequassinA = +19.9NNHOHOMeMeONNHOHOOMeOMeOHONHNCO2MeOHHOMeNNCO2MeOHHOAcMevinblastineA = +104.4cH"#$%&'!()+*5
!%U//\%).%5636,'6*%&2'+(23%=()*+,'5"%%?06%*1=)36%:):6&'5%).%'06%1&'6(2,-&9%
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'06%0631,1'4%>6'D66&%'06%,0():)=0)(65"%%%!!
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("%2&*%;1&>325-&6
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519&5"%d1&,6%'06%#R]I5B%U//\%025%>66&%+-31L6*%.)(%5'6(6),06:1,23%*6'6(:1&2-)&%).%:2&4%)'06(%
&2'+(23%=()*+,'5%,)&'21&1&9%,0():)=0)(65%5+,0%25B%6&)&65B%*16&65%2&*%2():2-,%06'6(),4,365%
')%&2:6%2%.6D"%%?06%6V2:=365%).%%!!
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)>56(;6*%519&23B%2&*%K%).%'06%)>56(;6*%519&23%2(6%=();1*6*"
HOBzHBzOBzOHBzOA = +94.9HBzOHOBzHOBzA = -56.8OBzHBzOOBzHOBzHOBzA = +39.8A:B:C:cR"#$%&'!()++5!!
d636,'6*%5'6()1*23%*1)35"%%X1'0%1&,(6251&9%*15'2&,6B%'06%U//\%2:=31'+*65%
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9()+=5%5+,0%25B%23,)0)35%)(%2:1&65B%,2&%>6%'06%:62&5%')%1&5'233%'06%(6M+151'6%,0():)=0)(65"%%
d'6()1*5%D6(6%6V'6&51;634%5'+*16*%+51&9%'06%*1>6&L)2'6%*6(1;2-;6%:6'0)*%.)(%U//\"%%K%56(165%).%
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2&936%>6'D66&%'06%,0():)=0)(65%(6:21&5%'06%52:6"%%?06%#Bc<*1)3%EKG%50)D5%'06%32(965'%U//\%
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HBzOOBzBz!Amplitudep-NO2Php-OMep-CNp-N(Me)215,10015,30020,40024,60030,400-10.7-15.5-26.4-35.4
-56.8eI"#$%&'!()+15
%%?06%,)((632-)&%).%6V-&,-)&%,)6j,16&'%E–G%D1'0%U//\%2:=31'+*6"%%K5%–%
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5%>6&L)2'6%9()+=5"%%!&%96&6(23B%25%
'06%6V-&,-)&%,)6j,16&'%1&,(62565%5)%*)65%'06%U//\%2:=31'+*6"'"%%%F1&2334B%.)(%;1,1&23%*1)35B%U//\%50)D5%2%*6=6&*6&,6%)&%'06%2&936%>6'D66&%'06%
,0():)=0)(65"%%?06%2:=31'+*6%).%'06%519&23%(62,065%2%:2V1:+:%D06&%'06%,0():)=0)(65%2(6%
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6V=6,'6*B%KB%D1'0%2&%2&936%).%#N
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1%=()*+,6*%'06%32(965'"'"%%HOBzOBzBzO! ! +15¡(for 1,2-diol)A = +23.1HBzOOBz! ! -60¡A = -39.9HOBzOBzMeO! ! -105¡A = -43.0A:B:C:e#"#$%&'!()+25
%%U//\%2:=31'+*65%02;6%2&%2&9+32(%*6=6&*6&,6"%%F)(%'0656%*1)35B%)&34%'06%
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($%%?06%'(1=06&43=)(=04(1&%D25%8&)D&%')%02;6%2%32(96%
NNNNPhPhPhOOOXOXX!Amplitudep-N(Me)215,00030,400440,000550,00013.613.624.424.4HTPPZn-TPPMTPP 
         M = HZn-TPP 
   M = ZnRij (†)No ECCD+21+193+270ec"#$%&'!()+35
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/66)*6)./'(%/0;(,7;("%%8,(%-(',70%(:'()%.:%',(2%:?Pb(+'(;%'*%,7;)*07:.:%?2;()%P/:.+%+*2;.3*2:%
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HNHNHNOHHOOOHNOHHHNHNII.1II.1(2 equiv)NNHNHNHHHOOII.2(25 equiv)TFA 
(0.1 equiv) N2, reflux, 15 min30%1. TFA 
(0.9 equiv)     CH2Cl2, N2, rt, 16 h2.  p-chloranil (3 equiv)     CH2Cl2, N2, rt, 2 h      12%5101520+++YY456&7&'(()*+''
&72',(:.:%*=%',(%?2:?P:3'?'(;%;.67))*-(',/2(%/2;%6*)6,7).2%-(',70%
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(:'()%4/:%;().D(;%=)*-%/%6)*+(;?)(%)(6*)'(;%P7%M.2;:(7%/2;%+*O4*)<():%@&+,(-(%!!"#C"
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+*?60.2G%.2%/2%(f*)'%'*%*P'/.2%',(%=)((%'4((9()%@
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/i(-6':%4.',%A1B%/2;%1BB%',(%=)((%'4((9()%4/:%2*'%.:*0/'(;%@&+,(-(%!!"QC"%%8,.:%4/:%2*'%
(23)(07%?2(>6(+'(;"%%d.',%*',()%'4((9()%:7:'(-:F%',(%7.(0;%*=%',(%=)((%'4((9()%+*?60.2G%.:%

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4/:%/23+.6/'(;%',/'%',(%:(+*2;%+*?60.2G%4*?0;%P(%(D(2%0*4()"%%!2%',.:%+/:(F%',(%:(+*2;%
Ye+*?60.2G%=/.0:%'*%6)*D.;(%',(%;(:.)(;%6)*;?+'"%%E*00*4.2G%',(%=/.0?)(%*=%',(%')/;.3*2/0%'4((9()%
:72',(:.:"%%\0'()2/3D(%6/',4/7:%'*%',(%'4((9()%4()(%(2D.:.*2(;"NNHNHNHHHOONNHNHNHHHOOHNaOH (2 M)THF, 
reflux, 12 hquantitative(Isolation ~10%)HOOHNNHNHNHHHOOOHII.2II.3II.3NNHNHNHHHOOOII.4NNHNHNHHHOII.5(1.3 equiv)EDC (1.3 equiv)DMAP 
(1.3 equiv)CH2Cl2, N2, rt, 4 d10%(1.3 equiv)EDC (1.3 equiv)DMAP 
(1.3 equiv)CH2Cl2, N2, rt, 12 hYU456&7&'(()/+
%%\i(-6'(;%:72',(:.:%*=%',(%?2:?P:3'?'(;%6*)6,7).2%'4((9()%4.',%',(%
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'*%/D*.;%/a?(*?:%)(/+3*2%+*2;.3*2:%4/:%;(:.)(;"%%\:%/%6*'(23/0%:*0?3*2F%',(%?2:?P:3'?'(;%
6*)6,7).2%P(2970%(:'()%4/:%;(:.G2(;"%%]20.<(%',(%-(',70%(:'()F%',(%P(2970%(:'()%+*?0;%P(%
;(6)*'(+'(;%?2;()%,7;)*G(2*07:.:%+*2;.3*2:%'*%7.(0;%',(%/+.;"%%S2+(%',(%)(/+3*2%.:%+*-60('(F%

V0')/3*2%+*?0;%/00*4%=*)%:(6/)/3*2%*=%',(%/+.;%=)*-%',(%-('/0%+/'/07:'"%%!2%',.:%4/7F%',(%/+.;%
4*?0;%P(%*P'/.2(;%4.',*?'%P(.2G%(>6*:(;%'*%/2%/a?(*?:%(2D.)*2-(2'"%%&72',(:.:%*=%',(%
?2:?P:3'?'(;%6*)6,7).2%P(2970%(:'()%P(G/2%4.',%',(%:72',(:.:%*=%KO=*)-70%P(2970P(29*/'(%@
(()3
F%
&+,(-(%!!"`C%=)*-%KO=*)-70%P(29*.+%/+.;%/2;%P(2970P)*-.;("%%8,(%+*2;(2:/3*2%*=%
;.67))*-(',/2(F%67))*0(OQO+/)P*>/0;(,7;(%/2;%',(%P(2970P(29*/'(%/2;%:?P:(a?(2'%*>.;/3*2%
6)*D.;(;%',(%;(:.)(;%6*)6,7).2%P(2970%(:'()%@(()8
C%.2%#Ln%7.(0;"
HNHNHNOHHOOO(2 equiv)NNHNHNHHHOOII.7HOOOHOOOHBr(1.1 equiv)II.6II.1II.6K2CO3 (2 equiv)tBuNH3I (0.1 equiv)THF, 
reflux, N2, 12 h95%1. TFA 
(0.9 equiv)     CH2Cl2, N2, rt, 16 h2.  p-chloranil (3 equiv)     CH2Cl2, N2, rt, 2 h      10%+++YR456&7&'(()0+
%%&72',(:.:%*=%',(%?2:?P:3'?'(;%6*)6,7).2%P(2970%(:'()"%d.',%
(()8
%.2%,/2;F%',(%,7;)*G(2*07:.:%4/:%/i(-6'(;%?2;()%/%D/).('7%*=%)(/+3*2%
+*2;.3*2:%@8/P0(%!!"#C"%%B*--*207F%,7;)*G(2*07:.:%.:%+*2;?+'(;%4.',%6/00/;.?-%*2%+,/)+*/0%@5;o
BC%/2;%,7;)*G(2"%%8,()(=*)(F%',(:(%4()(%',(%V):'%+*2;.3*2:%?:(;"%%]2=*)'?2/'(07F%.2%
;.+,0*)*-(',/2(%/%;(+*-6*:.3*2%6)*;?+'%4/:%.:*0/'(;%/:%',(%-/b*)%6)*;?+'"%%Z(>'F%',(%

:*0D(2'%4/:%+,/2G(;"%%\G/.2F%.2%(',70%/+('/'(%/2;%(',/2*0F%/%:.2G0(%;(+*-6*:.3*2%6)*;?+'%4/:%
NNHNHNHHHNNHNHNHHHOOOHOII.7II.3Desired ProductCatalystSolventH2 SourceResultEntry1Pd/CPd(OH)2EtOAcEtOAcEtOHEtOHEtOHEtOHPd/CPd/CPd/CH21,4-cyclohexadiene1,4-cyclohexadieneNo ReactionNo Reaction CH2Cl2 CH2Cl2Pd(OH)2Pd(OH)2Pd(OH)2H2H2H2H2H26785432NNHNHNHHHOOII.8II.8II.8II.8II.8II.8II.8ConditionsYX9:;<&'(()*+
%%N7;)*G(2*07:.:%*=%',(%?2:?P:3'?'(;%6*)6,7).2%P(2970%(:'()"%%\00%)(/+3*2:%)'F%
L"LLK%^%@:?P:')/'(CF%N
$%P/00**2F%#L%-*0n%+/'/07:'F%#%,*?)"
.:*0/'(;"%%!2'()(:32G07F%',(%Z^h:%*=%',(%.:*0/'(;%:
6(+.(:%4/:%',(%:/-(%=*)%/00%',)((%)(/+3*2:"%%
_7%Z^hF%.'%4/:%;('()-.2(;%',/'%',.:%6)*;?+'%)('/.2(;%',(%P(2970%(:'()%,*4(D()F%:(D()/0%
/)*-/3+%6(/<:%*=%',(%6*)6,7).2%-*D(;%?6V(0;"%%8*%6)(D(2'%',(%*D()O)(;?+3*2%*=%',(%
6*)6,7).2F%P*',%',(%+/'/07:'%/2;%',(%,7;)*G(2%:*?)+(%4()(%+,/2G(;"%%E.):'F%/%0(::%/+3D(%
ROODBU (0.5 equiv)LiBr (5 equiv) N2, rt, 24 hHOOH(10 equiv)LiBr (10 equiv)CH2Cl2, N2, rt, 24 hHOOHII.7NNHNHNR =OOROOOHII.7RII.4ROOII.2(7 equiv)I2 (12 equiv) N2, rt, 24 hHOOHROOII.2H2SO4 (10 equiv) N2, 55 ¡C, 24 h30%HOOHHHHeL456&7&'(()1+'
\i(-6'(;%')/2:(:'().V+/3*2%)(/+3*2:%'*%G(2()/'(%',(%?2:?P:3'?'(;%6*)6,7).2%-*2*0.2<()%=)*-%',(%P(2970%/2;%-(',70%(:'():"6/00/;.?-%+/'/07:'F%5(/)0-/2g:%+/'/07:'%@5;@SNC
$oBCF%4/:%(-60*7(;"%%S2+(%/G/.2%*D()O)(;?+(;%
6)*;?+'%4/:%.:*0/'(;"%%!2%/%V2/0%/i(-6'F%/%0(::%/+3D(%,7;)*G(2%:*?)+(%4/:%?:(;"%%N*4(D()F%2*%
)(/+3*2%4/:%*P:()D(;%4.',%#FKO+7+0*,(>/;.(2("%%E?)',()%/2/07:.:%*=%',(%?2;(:.)(;%6)*;?+'%
.2;.+/'(;%',/'%',(%'4*%;*?P0(%P*2;:%.2%',(%6*)6,7).2%',/'%/)(%+)*::O+*2b?G/'(;%4.',%',(%

/)*-/3+%:7:'(-%/)(%,7;)*G(2/'(;%?2;()%',(:(%+*2;.3*2:"%%8,(:(%+)*::%+*2b?G/'(;%;*?P0(%
P*2;:%*=%',(%6*)6,7).2%,/D(%P((2%',(%'/)G('%*=%,7;)*G(2/3*2
$#"$-F%*>.;/3*2
$."##F%1.(0:O
\0;()
#)"#-%/2;%#F`O;.6*0/)%+7+0*/;;.3*2
#.")-%)(/+3*2:%'*%7.(0;%+,0*).2:%/2;%P/+'().*+,0*).2:"%%
8,()(=*)(F%',(%?2;(:.)(;%)(;?+3*2%.:%0.<(07%?2/D*.;/P0(%/2;%',.:%)*?'(%4/:%/P/2;*2(;"

%E*00*4.2G%',(%;(P(2970/3*2%/i(-6':F%')/2:(:'().V+/3*2%*=%',(%?2:?P:3'?'(;%
6*)6,7).2%(:'()%4/:%(>60*)(;%/:%/%-(/2:%*=%;.)(+'07%:72',(:.9.2G%',(%-*2*0.2<()%',()(P7%

+.)+?-D(232G%',(%?2:?P:3'?'(;%6*)6,7).2%/+.;"%%\'%V):'%',(%-(',70%/2;%P(2970%(:'():%4()(%
:?P-.i(;%'*%')/2:(:'().V+/3*2%+*2;.3*2:"%%_*',%M(4.:%P/:(%-(;./'(;%/2;%P/:(%+/'/079(;%
@&+,(-(%!!"KC%+*2;.3*2:%4()(%?:(;%4.',%2*%:?++(::"
).(),%%\+.;%+/'/079(;%+*2;.3*2:%4()(%
-*;()/'(07%:?++(::=?0%P?'%*207%.=%',(%/0+*,*0%4/:%',(%:*0D(2'"
*/%%8,(%0.-.'(;%:?++(::%*=%',(:(%
-(',*;:%4()(%/i).P?'(;%'*%',(%0(/D.2G%G)*?6%*=%',(%(:'()"%%!2%P*',%+/:(:F%/2%/0<70%/0+*,*0%@#FYO
6(2'/2(;.*0C%-?:'%;.:60/+(%/2%/0<70%/0+*,*0%@P(2970%/0+*,*0%*)%-(',/2*0C"%%8,(%0(/D.2G%G)*?6%
/P.0.'7%=*)%/00%',)((%/0+*,*0:%:,*?0;%P(%/66)*>.-/'(07%',(%:/-(%',()(=*)(F%',()(%.:%2*%;).D.2G%

=*)+(%=*)%',(%)(/+3*2%'*%6)*+((;%?20(::%',(%#FYO6(2'/2(%;.*0%.:%6)(:(2'%.2%0/)G(%(>+(::%@/:%',(%
:*0D(2'C"%%8*%.-6)*D(%',(%0(/D.2G%G)*?6%/P.0.'7%*=%',(%(:'()%/0+*,*0F%',(%?2:?P:3'?'(;%6,(270%
(:'()%4/:%:72',(:.9(;"%%E*)%',(%6,(270%(:'()F%6,(2*0%.:%',(%/0+*,*0%P(.2G%;.:60/+(;%P7%',(%#FYO

6(2'/2(%;.*0"%%5,(2*0%.:%/%P(i()%0(/D.2G%G)*?6%',/2%',(%;.*0%',()(=*)(F%',(%')/2:(:'().V+/3*2%
:,*?0;%6)*+((;%'*%G(2()/'(%',(%;(:.)(;%-*2*0.2<()%6)*;?+'"%%&72',(:.:%*=%',(%6,(270%(:'()%
e#P(G/2%4.',%/2%A1B%-(;./'(;%+*?60.2G%*=%
KO=*)-70P(29*.+%/+.;%/2;%6,(2*0%'*%6)*D.;(%KO=*)-70%
6,(270P(29*/'(%@
(()=
F%&+,(-(%!!"YC"%%8,(%P(29*/'(%
(()=
%4/:%',(2%:?Pb(+'(;%'*%/+.;%+/'/079(;%
+*2;(2:/3*2%4.',%;.67))*-(',/2(%
(()/
%/2;%67))*0(OQO+/)P*>/0;(,7;(%7.(0;.2G%',(%;(:.)(;%
?2:?P:3'?'(;%6,(270%(:'()%.2%`n%7.(0;"HNHNHNOHHOOO(2 equiv)NNHNHNHHHOOII.10HOOOHOOOHOH(1.3 equiv)II.9II.1II.91. TFA 
(0.5 equiv)     CH2Cl2, N2, rt, 16 h2.  p-chloranil (3 equiv)     N2, rt, 2 h, 3%DCC (1.3 equiv)DMAP 
(1.3 equiv)CH2Cl2, N2 rt, 12 h78%+++NNHNHNHHHOOII.10NNHNHNHHHOOOHII.4(excess)NaH (10 equiv)THF, 
 N2, rt, 4 h94%HOOHeQ456&7&'(()2+
%&72',(:.:%*=%KO=*)-706,(270P(29*/'(%/2;%?2:?P:3'?'(;%6*)6,7).2%6,(270%
(:'()"%8,(%')/2:(:'().V+/.*2%*=%',(%6,(270
%(:'()%4.',%#FYO6(2'/2(;.*0%?2;()%P/:.+%+*2;.3*2:F%
:*;.?-%,7;).;(%@Z/NCF%6)*+((;(;%.2%,.G,%7.(0;%@8/P0(%!!"QC"%%A2+*?)/G(;%P7%',.:%)(:?0'F%/%:(+*2;%
')/2:(:'().V+/3*2%*=%',(%-*2*0.2<()%4.',%',(%6*)6,7).2%6,(270%(:'()%4/:%/i(-6'(;%'*%G.D(%',(%
'4((9()"%%!2%/00%+/:(:F%',(%;(:.)(;%'4((9()%4/:%2*'%G(2()/'(;p%.2:'(/;F%',(%:'/)32G%-/'()./0:%

4()(%.:*0/'(;"%%E(/).2G%',/'%',(%P/:(%4/:%P(.2G%+*2:?-(;%P7%;(6)*'*2/32G%',(%6*)6,7).2F%',(%
')/2:(:'().V+/3*2%4/:%/i(-6'(;%4.',%',(%9.2+/'(;%-*2*0.2<()%/2;%',(%9.2+/'(;%6,(270%(:'()"%%
NNNNOOBaseSolventEntry12 HZnKHMDS/HMPA
KHMDS/HMPA
NaHKHMDS/HMPA
a2 H2 HTHFNaH
NaHZnTHFTHFCH2Cl2THF65432MNNNNOOOHMConditionsNNNNOOONNNNOMMMZnTHFHHHHHHHHHHHH+M = 2H (II.10)M = Zn (II.11
)M = 2H (II.4)M = Zn (II.12)M = 2H (II.5)M = Zn (II.13)e`9:;<&'(()/+''
]2:?++(::=?0%')/2:(:'().V+/3*2%)(/+3*2:%'*%7.(0;%',(%6*)6,7).2%'4((9()"%%\00%)(/+3*2:%/'%)'F%?2;()%Z
QF%0/)G(%(>+(::%*=%P/:(F%R,"%/$%QL%(a?.D%;.P(29*O#RO+)*42Oe%(',()"
\G/.2%',(:(%)(/+3*2:%4()(%?2:?++(::=?0"%%8,(%=/.0?)(%*=%',(%')/2(:'().V+/3*2%'*%7.(0;%',(%
'4((9()%+*?0;%P(%;?(%'*%'4*%=/+'*):$%#"%',(%)(/+3*2%+*2+(2')/3*2%/2;%Q"%0*+/0%+*2+(2')/3*2%*=%
',(%2?+0(*6,.0("%%8,(%')/2:(:'().V+/3*2%7.(0;.2G%',(%-*2*0.2<()%.:%+*2;?+'(;%4.',%/%0/)G(%
(>+(::%*=%',(%;.*0%',()(=*)(F%.2+)(/:.2G%',(%6)*P/P.0.'7%*=%',(%;(6)*'*2/'(;%;.*0%/2;%',(%6,(270%

(:'()%-((32G%.2%:*0?3*2"%%E*)%',(%:(+*2;%')/2:(:'().V+/3*2F%/%#$#%)/3*%*=%-*2*0.2<()%
2?+0(*6,.0(%/2;%6,(270%(:'()%-?:'%P(%?:(;%;?(%'*%',(%0.-.'(;%a?/233(:%*=%',(%6*)6,7).2:%
/D/.0/P0(%',?:%)(;?+.2G%',(%6)*P/P.0.'7%*=%',(%'4*%-((32G"%%\:%/2%/;;.3*2/0%+*-60.+/3*2F%

4,(2%',(%-*2*0.2<()%.:%;(6)*'*2/'(;F%',(%/0<*>.;(%=*)-(;%.:%:.>%/'*-:%=)*-%/2%(:'()%
=?2+3*2/0.'7"%%8,(%.2')/-*0(+?0/)%/i/+<%*=%',(%/0<*>.;(%*2%',(%(:'()%+*?0;%*++?)%;?(%'*%/2%
.2+)(/:(;%0*+/0%+*2+(2')/3*2%*=%',(%2?+0(*6,.0("%%8,.:%)(/+3*2%+*?0;%:0*4%*)%6)(D(2'%',(%

')/2:(:'().V+/3*2%=)*-%*++?)).2G%P7%?:.2G%',(%/0<*>.;(%.2%?26)*;?+3D(%6/',4/7:"NNHNHNHHHOOONNHNHNHHHONHHNOOONHHNONHHNHOHOeK!"#$%&'(()8+'
h(')*:72',(:.:%*=%',(%?2:?P:3'?'(;%6*)6,7).2%'4((9()%:60.q2G%',(%'4((9()%
.2'*%'*6%/2;%P*i*-%,/0D(:"%\%V2/0%/i(-6'%'*%',(%?2:?P:3'?'(;%
6*)6,7).2%'4((9()%.2D*0D(;%:60.q2G%',(%'4((9()%.2%
,/0=%',)*?G,%',(%6*)6,7).2:%@E.G?)(%!!"UC"%%8,(%'*6%/2;%P*i*-%,/0D(:%4*?0;%P(%:72',(:.9(;%
:(6/)/'(07%4.',%',(%6*)6,7).2%+*2;(2:/3*2%0(c%'*%',(%0/:'%:'(6"%%8,(%P(2(V'%'*%',.:%)*?'(%.:%
',/'%',(%+*?60.2G%)(/+3*2:%'*%.2:'/00%',(%-(',70(2(%0.2<()%4*?0;%P(%+*-60('(;%4.',%',(%

+*--()+./007%/D/.0/P0(%KO=*)-70P(29*.+%/+.;%4,.+,%.:%-*)(%:*0?P0(%.2%*)G/2.+%:*0D(2':%',/2%',(%6*)6,7).2%/+.;"%%8*%P?.0;%',(%'*6%,/0=F%',(%;.67))*-(',/2(F%
(()*
F%4/:%:?Pb(+'(;%'*%/%-*;.V(;%
r.0:-(7()ON//+<%=*)-70/3*2
%'*%=*)-%',(%YFYgO;.=*)-70OQFQgO;.67))*-(',/2(F%
(()*1
F%.2%)/',()%0*4%
7.(0;:"
*!(*$%%%&72',(:.:%*=%',(%P*i*-%,/0=%P(G/2%4.',%',(%:(a?(23/0%A1B%+*?60.2G:%*=%KO

=*)-70P(29*.+%/+.;%'*%#FYO6(2'/2(%;.*0%'*%7.(0;%6(2'/2(O#FYO;.70%P.:@KO=*)-70P(29*/'(CF%
(()*3
"%%
Z(>'F%+*2;(2:/3*2%4.',%67))*0(%G/D(%',(%P.:O;.67))*-(',/2(F%
(()*8
F%'*%=*)-%',(%P/:(%*=%',(%
'4((9()"%%8,(%+*2;(2:/3*2%*=%
(()*1
%/2;%
(()*8
F%.=%:?++(::=?0F%4*?0;%,/D(%G(2()/'(;%',(%
-('/00/'(;%'4((9()"%%8,(%'76.+/0%7.(0;%=*)%',(%:72',(:.:%*=%/%:.2G0(%6*)6,7).2%.:%'76.+/007%#LOQLn"%%
N*4(D()F%.2%',.:%+/:(%',(%:72',(:.:%4*?0;%+)(/'(%'4*%6*)6,7).2:%/2;%:*%',(%7.(0;%4*?0;%;)*6%'*%

#OKn"%%8,(%6)*;?+'F%.=%=*)-(;%+*?0;%2*'%P(%.:*0/'(;"%%8,.:%'4((9()%4/:%/P/2;*2(;%;?(%'*%',(%
:72',(3+%.::?(:"HNHNNHNHHOHOClODMF (12 equiv)N2, rt, 4 h25%II.1II.14(5 equiv)+eY456&7&'(()3+
%&72',(:.:%*=%YFYgOP.:%=*)-70OQFQgO;.67))*-(',/2("
HOOOHHO(1.3 equiv)EDC (1.3 equiv)DMAP 
(1.3 equiv)CH2Cl2, N2, rt, 24 h82%OHHOOOOHHOOOHHOOOOOOHNH(25 equiv)TFA 
(0.1 equiv)N2, rt, 30 min30%NNNNHHHOONNNNHHHOOZn(OAc)2 (10 equiv)nPrNH2 (0.15 equiv) EtOH, air, 
reflux, 16 hMMII.15(2 equiv)+(1.3 equiv)EDC (1.3 equiv)DMAP 
(1.3 equiv)CH2Cl2, N2, rt, 24 h70%II.16OOOONHHNNHHNII.17OOOONHHNNHHNII.17NHNHHOHOII.14DBU (10 equiv)MgBr2 (3 equiv)toluene, reflux, 19 hII.18M = Zn or Mgee456&7&'(()8+''
\i(-6'(;%:72',(:.:%*=%',(%?2:?P:3'?'(;%'4((9()"!!"K$%1(:.G2%/2;%&72',(:.:%*=%',(%5()j?*)*/0<70%5*)6,7).2%84((9()%E)*-%',(%)(:?0':%*=%',(%:'().+%/2;%(0(+')*2.+%'?2.2G%*=%',(%6*)6,7).2F%/%:().(:%*=%s:?6()O
'4((9():t%4()(%6)*6*:(;"%%S=%',(:(%:?GG(:'(;%'4((9():F%',(%
'()*
%6()j?*)*/0<70%6*)6,7).2%
'4((9()F%[2OB
#E-O84((9()%@[2OB
#E-O89CF%4/:%.2'(2;(;%'*%:()D(%/%;?/0%6?)6*:(%@E.G?)(%!!"RF%^(%
A:'()%.:%:,*42C"%%E.):'F%',.:%'4((9()%4/:%;(:.G2(;%'*%'(:'%*?)%,76*',(:.:%',/'%:?P:')/'(%P.2;.2G%

/H2.3(:%+/2%P(%+*))(0/'(;%'*%',(%A
0123%(2()G.(:%*=%',(%9.2+%+(2'()%*=%',(%6*)6,7).2"%%
&6(+.V+/007%',/'%P.2;.2G%/H2.3(:%/)(%,.G,()%=*)%'4((9():%4.',%0*4()%A
0123%(2()G7"%%_(.2G%',/'%
',(%M]^S%(2()G7%*=%',(%[2OB
#E-O84((9()%.:%0/)G()%',/2%P*',%[2O855O84((9()%/2;%[2O85E5O
84((9()F%:-/00()%P.2;.2G%/H2.3(:%/)(%/23+.6/'(;"%%&(+*2;F%',.:%'4((9()%;.f():%=)*-%/00%*',():%

.2%',/'%',)((%*=%',(%
'()*
%:?P:3'?(2':%/)(%/0<70%+,/.2:"%%\0<70%+,/.2:%,/D(%-*)(%;(G)((:%*=%
=)((;*-%',/2%;*%6,(270%).2G:%/2;%.'%4/:%(>6(+'(;%',/'%4.',%/%:?P:')/'(%P*?2;F%',.:%+,/.2%
4*?0;%)*'/'(%*?'%*=%',(%P.2;.2G%6*+<('%*=%',(%'4((9()%'*%-.2.-.9(%.2'()/+3*2:%4.',%',(%
:?P:')/'("%%_7%-.2.-.9.2G%,*:'OG?(:'%.2'()/+3*2:F%',(%')/2:=()%*=%6*.2'%+,.)/0.'7%*=%',(%:?P:')/'(%
NNNNRRRZnCO2MeFFFFFR =ELUMO (eV) =3.932.57FFFFFFFKa iPrOH (M-1)=492,1704.54?Zn-TPPZn-TPFPZn-C3F7eU!"#$%&'(()>+
%&')?+'?)(:%*=%',(%[2O855F%[2O85E5%/2;%[2O
B#E-%^(%A:'():"%%A
0123%/2;%
P.2;.2G%+*2:'/2':%@4.',%.:*6)*670%/0+*,*0C%.2;.+/'(%/:%',(%(2()G7%*=%',(%M]^S%;)*6:F%
P.2;.2G%/H2.'7%.2+)(/:(:"'*%,(0.+/0%+,.)/0.'7%*=%',(%'4((9()%:,*?0;%P(%.2(H+.(2'%/'%P(:'"%%
8,?:F%/27%ABB1%:.G2/0:%*P:()D(;%
:,*?0;%P(%*=%:-/00()%/-60.'?;(%4.',%',.:%'4((9()%/:%+*-6/)(;%'*%[2O855O84((9()%*)%[2O85E5O
84((9()"%%8,(%+*-6/).:*2%*=%ABB1%)(:?0':%4.',%',(:(%',)((%'4((9():%:,*?0;%(0?+.;/'(%',(%)*0(%
*=%',(%6,(270%).2G:%.2%+,.)/0.'7%')/2:=()"
%E*)%',.:%:'?;7F%',(%#LF#YFQLO').:@QFQF`F`FKFKFKO,(6'/j?*)*6)*670COYO@KOP(29*/'(C
6*)6,7).2%4/:%;(:.G2(;%'*%'/<(%/;D/2'/G(%*=%',(%+*--()+./007%/D/.0/P0(%/0;(,7;("%%8,(%
:72',(:.:%*=%',(%6()j?*)*/0<70%'4((9()%4/:%;(:.G2(;%'*%=*00*4%',(%6)*+(;?)(%;(D(0*6(;%=*)%',(%

:72',(:.:%*=%85E5%'4((9()"
!,%%[.2+/3*2%*=%',(%=)((%B
#E-O'4((9()%4*?0;%6)*D.;(%[2OB
#E-O84((9()F%',(%,*:'%:7:'(-%=*)%ABB1%/2/07:.:"%%8,(%=)((%'4((9()%.:%',(%6)*;?+'%*=%:(a?(23/0%ABB1%
+*?60.2G:%*=%',(%B
#E-%6*)6,7).2%/+.;%/2;%#FYO6(2'/2(%;.*0"%%8,(%/+.;%4*?0;%P(%*P'/.2(;%=)*-%
,7;)*07:.:%*=%',(%B#E-%-(',70%(:'()"%%%\i(-6':%'*%:72',(:.9(%',(%,(6'/j?*)*6)*6706*)6,7).2%-(',70%(:'()%@
(()*=
C%P7%
+*2;(2:/3*2%*=%KO=*)-70-(',70%P(29*/'(F%67))*0(%/2;%6()j?*)*P?'7)0/0;(,7;(%,7;)/'(%
=*00*4.2G%',(%6)*+(;?)(%=*)%:72',(:.:%*=%85E5%-(',70%(:'()%4()(%0/)G(07%?2:?++(::=?0"%%N*4(D()F%

?2;()%-*;.V(;%)(/+3*2:%+*2;.3*2:F%',.:%-(',*;%6)*D.;(;%',(%
+,$%)%;.-(',70%(:'()%6*)6,7).2%
@(()/?
C%/:%',(%-/b*)%6)*;?+'%@8/P0(%!!"`C"%%8,.:%4/:%?2=*)'?2/'(%+*2:.;().2G%',/'%
(()*=
%.:%)(a?.)(;%
=*)%+*2:')?+3*2%*=%',(%'4((9()"%%!'%4/:%)(/:*2(;%',/'%',(%/0;(,7;(%*=%KO=*)-70%-(',70%

P(29*/'(%.:%0.<(07%-*)(%)(/+3D(%',/2%,7;)/'(;%/0;(,7;(%*=%',(%6()j?*)*P?'7/0;(,7;("%%
8,()(=*)(F%',(%67))*0(%.:%0.<(07%)(/+32G%6)(=()(23/007%4.',%',(%P(29*/'(%/2;%6)(D(232G%
=*)-/3*2%*=%',(%;(:.)(;%6*)6,7).2"%%8*%)(-(;7%',.:%6)*P0(-F%',(%6()j?*)*P?'7).+%,7;)/'(%/2;%

',(%67))*0(%4()(%/00*4(;%'*%)(/+'%.2%',(%6)(:(2+(%*=%P*)*2%').j?*).;(%;.(',70%(',()/'(%
@_E#4SA'$C%=*)%K%,*?):%6).*)%'*%',(%/;;.3*2%*=%',(%-(',70%KO=*)-70P(29*/'("%%]2;()%',(:(%
eR+*2;.3*2:F%',(%;(:.)(;%6)*;?+'%4/:%.:*0/'(;F
%,*4(D()%.2%0*4%7.(0;"%%E.2/007F%0(2G',(2.2G%',(%
)(/+3*2%3-(%/2;%+,/2G.2G%',(%*>.;/2'%'*%11u%;*?P0(;%',(%7.(0;%'*%Yn"%8,(%7.(0;:%*=%6*)6,7).2%:72',(:(:%/)(%'76.+/007%a?.'(%0*4%P?'%Yn%7.(0;%4/:%?2/++(6'/P0(%%
=*)%G(2()/32G%',(%/-*?2'%*=%6*)6,7).2%)(a?.)(;%'*%+*232?(%4.',%',(%'4((9()%:72',(:.:"%%

8,()(=*)(F%/2*',()%)*?'(%4/:%;(:.)(;"%%8,(%:72',(:.:%*=%',(%;(:.)(;%6*)6,7).2%-(',70%(:'()%4/:%
NHC3F7OHOH1. BF3¥OEt2    (0.8 equiv)    CH2Cl2, N2    rt, time2. oxidant    CH2Cl2, N2    rt, 2 hHOOO(3 equiv)(4 equiv)NNHNHNC3F7C3F7OOOONNHNHNC3F7C3F7C3F7OO!!!II.19C3F7 Methyl EsterII.20Time 
(h)OxidantYield 
% (19/20)Entry1p-chloranilDDQd432p-chloranilp-chloranil0/30/72/125/nd22a6b38ceX9:;<&'(()0+'
!2.3/0%*63-.9/3*2%*=%B
#E-%-(',70%(:'()%:72',(:.:"%%/$%P(29*/'(%/;;(;%/c()%
`L%-.2"%P$%P(29*/'(%/;;(;%/c()%Q%,*?):"%+$%P(29*/'(%/;;(;%/c()%#R%,*?):"%;$%/;;(;%.2%
QF%#%(a?.D%6*)3*2:"%%E.):'%'*%)(/+3*2%-.>'?)(%=*)%#R%,*?):%',(2%'*%V0')/'(%;.::*0D(;%.2%
'*0?(2(F%)(j?>(;%=*)%KR%,*?):"
)(6*)'(;%P7%^**)(%/2;%+*4*)<():%.2%QLLK"
*#%%&7
2',(:.:%*=%',(%6*)6,7).2%-(',70%(:'()%=*00*4.2G%
',.:%6)*+(;?)(%)(a?.)(;%',/'%',(%;.67))*-(',/2(%*=%,(6'/j?*)*6)*670/0;(,7;(%,7;)/'(%@
(()/*
C%4/:%V):'%:72',(:.9(;"%%E*00*4.2G%',(%)(6*)'(;%+*2;(2:/3*2%4.',%+/'/073+%,7;)*+,0*).+%/+.;F%
/0+*,*0%
(()/*:
%4/:%.:*0/'(;%.2%/%ULn%7.(0;%)/',()%',/2%',(%;(:.)(;%;.67))*-(',/2("%%\%:+)((2.2G%
*=%0.'()/'?)(%)(6*)'(;%+*2;.3*2:%=*)%:72',(:.:%*=%;.67))*-(',/2(:%4/:%?2:?++(::=?0%/:%P*',%
').j?*)*/+(3+%/+.;%@8E\C
*)%/2;%.2;.?-%@!!!C%+,0*).;(%@!2B0
#C**%=/.0(;%@8/P0(%!!"KC"%%AD(2'?/007%/%
K`n%7.(0;%*=%',(%;(:.)(;%;.67))*-(',/2(%4/:%*P'/.2(;%4,(2%QL%(a?.D/0(2':%*=%,7;)*+,0*).+%

/+.;%+/'/07:'%4/:%?:(;"%%5)(:?-/P07F%/2%(>+(::%*=%/+.;%4/:%2(+(::/)7%'*%6)*-*'(%',(%
(0.-.2/3*2%*=%',(%,7;)*>70%G)*?6"
%8,(%;.67))*-(',/2(F%,(6'/j?*)*6)*670/0;,(7;(%,7;)/'(%/2;%KO=*)-70%-(',70%P(29*/'(%
4()(%',(2%:?Pb(+'(;%'*%_E
#4SA'$%+/'/079(;%+*2;(2:/3*2%/2;%:?P:(a?(2'%*>.;/3*2%4.',%11u%
=*)%/%'*'/0%*=%`e%,*?):"
*#%%d.',%',.:%6)*+(;?)(F%',(%-(',70%(:'()%4/:%*P'/.2(;F%,*4(D()%:300%/'%
0*4%7.(0;%@8/P0(%!!"YC"%%!-6)*D(-(2'%*=%',(%7.(0;F%4/:%/+,.(D(;%4,(2%',(%;.67))*-(',/2(%/2;%
CatalystSolventTime 
(min)Entry1THF432THF0070 (21a)43NHC3F7OHOHconditionsNHHNC3F7!NHC3F7OH!Yield 
(%)TFA
InCl3HClHClaneatneat15156060II.21II.21aUL9:;<&'(()1+'
S63-.9/3*2%*=%',(%
B#E-%;.67))*-(',/2(%:72',(:.:"%/$%QL%(a?.D%,7;)*+,0*).+%
/+.;"6()j?*)*6)*670%,7;)/'(%4()(%:?Pb(+'(;
%'*%+*2;(2:/3*2%=*)%K%,*?):%6).*)%'*%/;;.3*2%*=%',(%
P(29*/'("%%E.2/007F%:4.'+,.2G%',(%+/'/07:'%=)*-%_E
#4SA'$%'*%8E\%7.(0;(;%',(%6*)6,7).2%-(',70%
(:'()%/'%/%#Yn%7.(0;%4,.+,%.:%/2%.-6)*D(-(2'%*D()%',(%0.'()/'?)(%)(6*)'(;%en%7.(0;"*#%&+,(-(%!!"R%:?--/).9(:%',(%+*-60(3*2%*=%',(%:72',(:.:%*=%[2OB
#E-O84((9()%@
(()/2
C"%%
50(/:(;%4.',%',(%:72',(:.:%*=%
(()*=
F%',(%,7;)*07:.:%*=%',(%(:'()%'*%6)*D.;(%B
#E-%/+.;%@
(()//
C%4/:%
/+,.(D(;%?2;()%/+.;.+%+*2;.3*2:"%%8*%/::(-P0(%',(%B
#E-%-*2*0.2<()%@
(()/0
CF%.2.3/007%/2%/i(-6'%
'*%+*2D()'%',(%6*)6,7).2%/+.;%'*%',(%6*)6,7).2%/+70%+,0*).;(%=*00*4(;%P7%/;;.3*2%*=%#FYO6(2'/2(%
;.*0%4/:%6?):?(;%/:%',()(%4/:%0.'()/'?)(%6)(+(;(2+(%=*)%:72',(:.:%*=%',(%6*)6,7).2%/+70%
+,0*).;("
*#%%]2=*)'?2/'(07F%;(+*-6*:.3*2%*=%',(%6*)6,7).2%*++?))(;"%%\0'()2/3D(07F%',(%A1B%
C3F7OHOH1. Catalyst (0.8 equiv)    CH2Cl2, N2, rt, time2. DDQ (1 equiv)    CH2Cl2, N2, rt, 24 h3. DDQ (1 equiv)    toluene, N2, reflux, 12 hHOOO(2 equiv)NNHNHNC3F7C3F7C3F7OO!!Time 
(h)CatalystYield 
%Entry1BF3¥OEt232TFA
58151919aNHHNC3F7II.21II.1919aBF3¥OEt2U#9:;<&'(()2+'
E.2/0%*63-.9/3*2%*=%',(%B
#E-%-(',70%(:'()%@
(()*3
C%:72',(:.:"%%/$%P(29*/'(%
/;;(;%/c()%`%,*?):"NNHNHNCO2HC3F7C3F7C3F7NNHNHNC3F7C3F7C3F7OOOONNHNHNC3F7C3F7C3F7Zn(OAc)2 (excess)DMAP 
(4 equiv)CH2Cl2, rt, 24 hquanitative(1.3 equiv)EDC (1.3 equiv)DMAP 
(1.3 equiv) CH2Cl2, rt, 4 h75%HOOHNNNNC3F7C3F7C3F7OOOONNNNC3F7C3F7C3F7ZnZnNNHNHNC3F7C3F7C3F7OOOHNNHNHNCO2MeC3F7C3F7C3F7TFA
HCl reflux, 12 h65%II.19C3F7 Methyl Ester(1.3 equiv)EDC (1.3 equiv)DMAP 
(1.3 equiv) CH2Cl2, rt, 4 h76%II.1916II.23C3F7 MonolinkerII.24C3F7 Free Tweezer
II.22 C3F7 AcidII.25Zn-C3F7-Tweezer
UQ456&7&'(()>+'
&72',(:.:%*=%',(%[2OB#E-O84((9()%@(()/2
C"+/'/079(;%+*?60.2G%:(a?(2+(%4/:%?:(;"%%B*?60.2
G%*=%',(%
(()//
%/2;%#FYO6(2'/2(%;.*0%6)*D.;(;%
(()/0%/2;%',(%:?P:(a?(2'%+*?60.2G%*=%',(%
(()//
%4.',%
(()/0
%G/D(%',(%B
#E-%E)((%84((9()%@
(()/1
C%.2%YUn%
7.(0;%=*)%',(%'4*%:'(6:"%%8,(%9.2+/3*2%*=%',(%=)((%'4((9()%G/D(%a?/23'/3D(%7.(0;%*=%',(%[2O
B#E-O84((9()%@(()/2
C"!!"Y$%B*-6/)/3D(%ABB1%&'?;7%]:.2G%',(%5()j?*)*/0<70%5*)6,7).2%84((9()'d.',%',(%[2OB
#E-O84((9()%@
(()/2
C%.2%,/2;F%/2%ABB1%:'?;7%*=%+,.)/0%;./-.2(:F%/-.2*%
/0+*,*0:%/2;%;.*0:%4.',%',(%[2OB
#E-O84((9()F%[2O85E5O84((9()%/2;%[2O855O84((9()%4/:%
?2;()'/<(2"%%!=%',(%
'()*
%6,(270%:?P:3'?(2':%*=%',(%6*)6,7).2%/)(%)(a?.)(;%=*)%(H+.(2'%+,.)/0.'7%
)(+*G2.3*2F%',(%ABB1%/-60.'?;(:%4.',%[2OB
#E-O84((9()%:,*?0;%P(%+*2:.:'(2'07%:-/00()%',/2%[2O
85E5O84((9()%*)%[2O855O84((9()"%%\0:*F%.=%',(%3G,'()%P.2;.2G%.:%',(%)(:?0'%*=%',(%M]^S%(2()G.(:%
*=%',(%9.2+%+(2'()%*=%',(%6*)6,7).2:F%',(%+/0+?0/'(;%P.2;.2G%+*2:'/2':%=*)%/27%G.D(2%:?P:')/'(%
4.',%[2OB#E-O84((9()%:,*?0;%P(%:-/00()%',/2%[2O85E5O84((9()%*)%[2O855O84((9()"%%%8,(%:6(+')*6,*'*-(').+%/2/07:.:%P(G/2%P7%;('()-.2.2G%',(%/P:*)63*2%-/>.-?-%/2;%
',(%(>32+3*2%+*(H+.(2'%=*)%',(%[2OB
#E-O84((9()"%%8,.:%-(/:?)(-(2'%4/:%+*2;?+'(;%.2%
D/).*?:%:*0D(2':%@8/P0(%!!"eC"%%!2%,(>/2(:F%',(%:*0D(2'%?:(;%=*)%',(%ABB1%:'?;7F%',(%'4((9()%,/;%/%

T%&'%*=%KLX%2-%/2;%/2%(>32+3*2%+*(H+.(2'%*=%`#LFLLL%
M%-*0
"!%+-
"!%.2%,(>/2(:"%%8,(%
YF#LF#YFQLO'(')/<.:@,(6'/j?*)*6)*670C6*)6,7).2%.:%)(6*)'(;%'*%,/D(%/%T
%&'%*=%KLY2-%/2;%/2%
(>32+3*2%+*(H+.(2'%*=%#QLFLLL%
M%-*0
"!%+-
"!%.2%;.+,0*)*-(',/2("
*+%%\0:*F%6).*)%'*%ABB1%
/2/07:.:%*=%',(%:?P:')/'(O'4((9()%+*-60(>(:F%]rOr.:%3')/3*2:%*=%',(%[2OB
#E-O^(',70%(:'()%4.',%
)(0
OP?'70/-.2(%/2;%
+(,+
OP?'70/0+*,*0%4()(%+/)).(;%*?'"%%8,(:(%]rOr.:%3')/3*2:%6)*D.;(%P.2;.2G%
+*2:'/2':%=*)%/-.2(:%/2;%/0+*,*0:%4.',%',(%6*)6,7).2%-*2*-()%/2;%6)*D.;(%',(%-/>.-?-%
U`/P:*)P/2+(%:,.c%*=%',(%6*)6,7).2%4,(2
%',(%:?P:')/'(%.:%P*?2;"%%8,(%T
%&'%:,.c%D/0?(:%/)(%
.-6*)'/2'%=*)%+*-6/).:*2%4.',%',(%'4((9()%+*-60(>(:"%%d,(2%/%:?P:')/'(%P.2;:%'*%',(%-('/0%
+(2'()%*=%/%-('/00*6*)6,7).2F%',(%;*2/3*2%*=%(0(+')*2%;(2:.'7%+/?:(:%/%)(;%:,.c%*=%',(%T
%&'%=*)%
',(%6*)6,7).2"%%E*)%(>/-60(F%',(%P.2;.2G%*=%:(+OP?'70%/-.2(%'*%[2O855O^(',70%A:'()%+/?:(:%/%#Q%

2-%)(;%:,.c%*=%',(%/P:*)P/2+(%@E.G?)(%!!"X%\C"%%E*)%/%:?P:')/'(O'4((9()%+*-60(>%',(%*P:()D(;%
T%&'%:,.c%.:%',(%)(:?0'%*=%'4*%=/+'*):"
*-%%E.):'F%',(%;*2/3*2%*=%(0(+')*2%;(2:.'7%=)*-%',(%
:?P:')/'(%'*%',(%9.2+%+(2'():%*=%',(%6*)6,7).2:%+/?:(%/%)(;%:,.c"%%N*4(D()F%',()(%.:%/%+*-6(32G%
P0?(%:,.c%+/?:(;%P7%',(%6)*>.-.'7%*=%',(%6*)6,7).2:"%%d,(2%',(%+*-60(>%=*)-:F%',(%6*)6,7).2:%
/)(%P)*?G,'%+0*:(%'*%*2(%/2*',()%'*%P.2;%'*%',(%=?2+3*2/0%G)*?6:%*=%',(%:?P:')/'("%%_).2G.2G%',(%

6*)6,7).2:%+0*:(%'*%(/+,%*',()%+/?:(:%/%P0?(%:,.c%',/'%2(G/'(:%/%6*)3*2%*=%',(%)(;%:,.c%=)*-%
',(%;*2/3*2%*=%(0(+')*2:%'*%',(%-('/0%+(2'():"%%SD()/00F%/%)(;%:,.c%.:%*P:()D(;%=*)%',(%
:?P:')/'(O'4((9()%+*-60(>(:%/:%+*-6/)(;%'*%',(%'4((9()%/0*2("%%!'%.:%(>6(+'(;%',/'%',(%T
%&'%*=%',(%:?P:')/'(O-(',70%(:'()%+*-60(>%4.00%)(;O:,.c%-*)(%',/2%',(%T
%&'%=*)%',(%:?P:')/'(O'4((9()%
+*-60(>%/:%',(%-(',70%(:'()%+*-60(>%4.00%2*'%,/D(%',(%+*-6(32G%P0?(%:,.c"%%d,(2%',(%T
%&'%*=%Solvent!max (nm)310,000Hexanes409420,000413530,000417430,000MCH414Toluene
415CH2Cl2" (L 
M-1 cm-1)MeOH290,000UK9:;<&'(()3+
%&?--/)7%*=%]rOr.:%;/'/%=*)%',(%
[2OB#E-O84((9()"%%\00%-(/:?)(-(2':%#L
"+%^F%
)**-%'(-6()/'?)("/%:?P:')/'(O'4((9()%+*-60(>%.:%2(/)%',/'%*=%',(%:?P:')/'(O-(',70%(:'()%+*-60(>F%/%Q$#%+*-60(>%
.:%:?:6(+'(;%@E.G?)(%!!"X%_C"H2NNH2H3CHOOOOZnZnH2NNH2H3CHZn-TPP-Tweezer
!max = 414 nmZn-TPP-Methyl Ester!max = 414 nmOOZnH2NH2Nsec-butyl amineZn-TPP-Methyl Ester complex!max = 426 nm(1 equiv)1:1 (R)-1,2-diaminopropaneZn-TPP-Tweezer 
complex!max = 419 nmNH2H2NH3CHOOOOZnZnH2NNH2CH3HH2NNH2H3CH(excess)2:1 (R)-1,2-diaminopropaneZn-TPP-Tweezer 
complex!max = 426 nmA:B:UY!"#$%&'(()=+'
&?--/)7%*=%',(%/P:*)P/2+(%:,.c:%=*)%;.f()(2'%:?P:')/'(O6*)6,7).2%
+*-60(>(:"%
,+%_.2;.2G%*=%/2%/-.2(%'*%[2O855O^(',70%A:'()%+/?:(:%/%#Q%2-%)(;%:,.c"%
-+%#$#%P.2;.2G%*=%/%;./-.2(%'*%[2O855O84((9()%+/?:(:%/%:-/00()%)(;%:,.c%@R%2-C%',/2%',(%
Q$#%P.2;.2G%@#Q%2-C%;?(%'*%',(%+*-6(32G%P0?(%:,.c%+/?:(;%P7%',(%6)*>.-.'7%*=%',(%
6*)6,7).2:%.2%',(%#$#%+*-60(>"%&?Pb(+32G%B
#E-%^(',70%(:'()%@
(()*=
C%'*%9.2+%!!%/+('/'(%/2;%1^\5%6)*D.;(;%',(%[2OB
#E-O^(',70%A:'()%@
(()/3
C"%%]rOr.:%-*2.'*)(;%3')/3*2%*=%[2OB
#E-O^(',70%A:'()%4.',%
)(0
OP?'70/-.2(%/2;%
+(,+
OP?'70/0+*,*0%4/:%+*2;?+'(;"%%\;;.3*2%*=%',(%
)(0
OP?'70/-.2(%+/?:(;%/%#U%2-%:,.c%*=%
',(%/2;%/;;.3*2%*=%
+(,+
OP?'70/0+*,*0%+/?:(;%/%U%2-%:,.c"%%8,(%]rOr.:%4/:%-/2.6?0/'(;%=*)%
;('()-.2/3*2%*=%P.2;.2G%+*2:'/2':%@:((%(>6().-(2'/0%=*)%]rOr.:%3')/3*2%/2;%P.2;.2G%+*2:'/2'%
;('()-.2/3*2%G)/6,:C"%%8,(%P.2;.2G%+*2:'/2'%;('()-.2(;%4/:%.2%(>+(::%*=%#L
+%^"%%\2%/++?)/'(%
D/0?(%+*?0;%2*'%P(%+/0+?0/'(;%;?(%'*%',(%6**)%V'%*=%',(%(a?/3*2"%%8,(:(%0/)G(%P.2;.2G%+*2:'/2':%
:?66*)'%',(%,76*',(:.:%',/'%,.G,07%(0(+')*2%4.',;)/4.2G%:?P:3'?(2':%6)*-*'(%3G,'%6*)6,7).2O
:?P:')/'(%P.2;.2G"%
%8,(%ABB1%:'?;7%P(G/2%4.',%',(%/2/07:.:%*=%VD(%+,.)/0%;./-.2(:%4.',%/00%',)((%'4((9():"%%
8,(%;/'/%.:%:?--/).9(;%.2%8/P0(%!!"U"%%8,(%ABB1%;/'/%.:%)(6*)'(;%/:%',(%4/D(0(2G',%*=%',(%
B*i*2%(f(+'%4.',%',(%/-60.'?;(%*=%',/'%B*i*2%(f(+'%.2%6/)(2',(:.:"%%_7%+*2D(23*2F%',(%V):'%

B*i*2%(f(+'%.:%',(%-*)(%)(;%:,.c(;%:.G2/0%/2;%.:%0.:'(;%V):'%=*00*4(;%P7%',(%:(+*2;%B*i*2%
(f(+'%/2;%',(2%',(%*D()/00%/-60.'?;(%*=%',(%:.G2/0"%%8,(%(>6(+'(;%:.G2F%;('()-.2(;%=)*-%/%
6)(D.*?:07%(:'/P0.:,(;%-2(-*2.+F
*%=*)%(/+,%:?P:')/'(%.:%6)*D.;(;%/0*2G%4.',%/%Z(4-/2%
6)*b(+3*2%'*%(>60/.2%',(%(>6(+'(;%:.G2"%%E*)%(/+,%:?P:')/'(F%',(%:-/00%G)*?6%.:%,.G,0.G,'(;%.2%
)(;%/2;%',(%0/)G(%G)*?6%.2%P0?("%%d,(2%',(%6*)6,7).2%.:%P*?2;%'*%',(%+,.)/0%+(2'()F%.'%4.00%)*'/'(%
'*4/);%',(%:-/00%G)*?6%'*%)(;?+(%:'().+%.2'()/+3*2:"%%8,(%:(+*2;%6*)6,7).2%4.00%P.2;%*66*:.'(%

',(%0*+/3*2%*=%',(%V):'%6*)6,7).2%0(/;.2G%'*%/%,(0.+/0%/))/2G(-(2'"%%8,(%P*0;%/))*4%/P*D(%',(%
Z(4-/2%.2;.+/'(:%',(%,(0.+.'7%*=%',(%6*)6,7).2:%*2+(%',(%:?P:')/'(%,/:%P*?2;%'*%',(%'4((9()%
/2;%',(%6*:.3D(%*)%2(G/3D(%:.G2%/P*D(%',(%/))*4%.2;.+/'(:%',(%(>6(+'(;%:.G2"%%E*)%(D()7%

:?P:')/'(O'4((9()%+*-P.2/3*2F%',(%ABB1%:.G2/0%-/'+,(;%',(%(>6(+'(;%:.G2"%%E?)',()-*)(F%
Ue(2/23*-():%*=%/%:.2G0(
%+,.)/0%/-.2(%6)*D.;(;%ABB1%:.G2/0:%4.',%*66*:.'(%:.G2:"%%E.G?)(%!!"#L%.:%
/2%*D()0/7%*=%',(%ABB1%+?)D(:%=*)%',(%(2/23*-():%*=%#FQO;./-.2*+7+0*,(>/2(%4.',%(/+,%*=%',(%
'4((9():"%%\:%(>6(+'(;%',(%/-60.'?;(:%*P:()D(;%4.',%[2OB
#E-O84((9()%4()(%+*2:.;()/P07%
:-/00()%',/2%4.',%',(%*',()%'4*%'4((9():"Chiral DiamineNH2NH2NH2NH2NH2NH2NH2NH2NH2NH2Zn-TPFP-Tz! nm, ("#)426 (-66)414 (+42)A = -108429 (-197)417 (+158)A = -355426 (+64)413 (-38)A = +102430 (+209)417 (-137)A = +346-429 (+353)416 (-308)A = +661430 (-407)416 (+337)A = -744-432 (-111)
416 (+112)
A = -223431 (+151)417 (-135)A  =  +286Expected Sign427 (-82)413 (+47)A = -129427 (-294)414 (+224)A = -518Zn-TPP-Tz! nm, ("#)431 (-243)417 (+181)A = -424431 (+211)
420 (-151)A = +362434 (+271)419 (-287)A = +358434 (-242)419 (+274)A = -316432 (-132)417 (+138)A = -270Zn-C3F7-Tz! nm, ("#)Entry12345NH2PhHNH2PhH+NH2HPhNH2HPhH2NHHNH2H3CHNH2HNH2HNH2HNH2HII.27II.28II.29II.30II.31+-UU9:;<&'(()8+'
&?--/)7%*=%',(%ABB1%;/'/%=*)%;./-.2(:"%%\00%-(/:?)(-(2':$%,(>/2(:F%L%
5BF%
Q>#L"+%^%'4((9()F%#%(a?.D/0(2'%;./-.2("
%&*0D(2'%/2;%'(-6()/'?)(%:+)((2.2G%4.',%[2OB
#E-O84((9()%/2;%Q
"O;./-.2*6)*6/2(%4/:%
+*2;?+'(;%'*%(2:?)(%',/'%',(%*63-/0%+*2;.3*2:%4()(%.2%?:(%@8/P0(%!!"RC"%%\0',*?G,F%/'%)**-%
'(-6()/'?)(%',(%/-60.'?;(%=*)%',.:%6/)3+?0/)%:?P:')/'(%4/:%:0.G,'07%0/)G()F%L%
5B%4/:%?03-/'(07%
+,*:(2%/:%ABB1%/-60.'?;(:%/)(%<2*42%'*%;(+)(/:(%/'%)**-%'(-6()/'?)(%=*)%P*',%[2O85E5O

84((9()%/2;%[2O855O84((9()"
!.(!,%%ABB1%/-60.'?;(%.2%-(',70+7+0*,(>/2(%@^BNC%4/:%
+*-6/)/P0(%'*%,(>/2(:F%,*4(D()F%',(%/-60.'?;(:%4()(%:-/00()%/2;%2*.:.()%.2%;.+,0*)*-(',/2(%

/2;%'*0?(2("%%N(>/2(:%4/:%+,*:(2%=*)%',(%)(-/.2;()%*=%',(%:'?;7%/:%[2O85E5O84((9()
!,%/2;%
[2OB#E-O84((9()%6)*D.;(%:')*2G()%:.G2/0:%.2%,(>/2(:"-410!-310!-210!-110
!-10!90!190!290!Mol CD!Wavelength (nm)
!(S,S)-C3F7!(S,S)-TPP!(S,S)-TPFP!(R,R)-C3F7!(R,R)-TPP!(R,R)-TPFP!380420UR!"#$%&'(()*?+%SD()0/7%*=%ABB1%:6(+')/%=*)%#FQO;./-.2*+7+0*,(>/2(%4.',%',(%[2O84((9():"%%
\00%-(/:?)(-(2':$%,(>/2(:F%L%
5BF%Q>#L
"+%^%'4((9()F%#%(a?.D/0(2'%;./-.2("
%!2%/;;.3*2%'*%',(%/2/07:.:%P7%ABB1F%
(/+,%'4((9()O:?P:')/'(%+*-60(>%4/:%/2/079(;%P7%
]rOr.:%3')/3*2"%%\:%;(:+).P(;%/P*D(F%',(%]rOr.:%3')/3*2%6)*D.;(:%<(7%.2=*)-/3*2%:?+,%/:%',(%
'76(%*=%+*-60(>%=*)-(;%@."("%#$#%*)%Q$#%:?P:')/'($'4((9()C%P7%v*Pg:%60*'%/2/07:.:
*.(*,%/2;%
P.2;.2G%+*2:'/2':"
+/%%_*',%',(%v*Pg:%60*'%/2;%',(%P.2;.2G%+*2:'/2'%/)(%=*?2;%P7%+*-6/).:*2%*=%
',(%/P:*)P/2+(%:,.c%4.',%',(%/-*?2'%*=%:?P:')/'(%6)(:(2'"%%E.G?)(%!!"##%6)*D.;(:%',(%v*Pg:%60*'%

/2P.2;.2G%+*2:'/2'%+/0+?0/3*2%=*)%#FQ
"O;./-.2*6)*6/2("%%8,(%v*Pg:%60*'%+*))(0/'(:%4(00%4.',%/%
#$#%+*-60(>%/:%',(%/6(>%*=%',(%6/)/P*0/%.:%*P:()D(;%/'%/%-*0%=)/+3*2%*=%L"Y"%%\%P.2;.2G%+*2:'/2'%

*=%Q>#L
-%^%4/:%+/0+?0/'(;%=*)%',.:%:?P:')/'("%%8,(%P.2;.2G%+*2:'/2':%=*)%',.:%;./-.2(%4.',%[2O
855O84((9()%/2;%[2O85E5O84((9()%4()(%/0:*%+/0+?0/'(;"%%[2O855O84((9()%:,*4(;%',(%:-/00(:'%
SolventTemp 
(¡C)427 (-82)413 (+47)    A = -129Hexanes0427 (-87)415 (+53)    A = -140Hexanes10427 (-101)415 (+72)    A = -173Hexanesrt428 (-63)413 (+32)    A = -95MCH0432 (-12)415 (+10)    A = -22aToluene
0426 (+14)413 (-8)       A = +22a0Zn-C3F7-Tz! nm, ("#)CH2Cl2UX9:;<&'(()>+
%&*0D(2'%/2;%'(-6()/'?)(%:+)((2.2G%*=%
[2OB#E-O84((9()%/2;%@
"COQO;./-.2*6)*6/2("%\
00%-(/:?)(-(2':$%Q>#L
"+%^%'4((9()F%#%(a?.D/0(2'%;./-.2("%/$%`%
(a?.D/0(2':%;./-.2("0!0.01!0.02!0.03!0.04!0.05!0.06!0.07!0!0.2!0.4!0.6!0.8!1!Mol Frac Tz * ! Abs
!Mol Frac Tz!RL!"#$%&'(()**+'
_.2;.2G%;/'/%=*)%#FQ
"O;./-.2*6)*6/2(%4.',%[2O
B#E-O84((9()"%%
,+%v*Pg:%60*'%
.2;.+/32G%/%#$#%+*-60(>"%%-+'8,(%P.2;.2G%+*2:'/2'%+/0+?0/3*2"%%,+-+Chiral AminoAlcoholZn-TPFP-Tz! nm, ("#)428 (+115)
412 (-64)A = +179427 (+256)413 (-164)A = +420427 (-70)411 
(+52)A = -122427 (-198)413 (+136)A = -334+--428 (+163)419 (-126)A = +289a423 (+167)413 (-80)A = +247+430 (-15)415 (+52)A = -67425 (+101)414 (-47)A  =  +148aExpected Sign424 (+12)414 (-29)A = +41427 (-91)416 (+45)A = -136Zn-TPP-Tz! nm, ("#)432 (+296)416 (-229)A = +535431 (-181)417 (+159)A = -340430 (+260)421 (-190)A = +450a435 (-242)427 (+56)417 (-28)423 (-255)413 (+147)A = -402OHNH2NH2OHOHNH2OHNH2OHNH++NH2OHOHN423 (+17)415 (-20)A = +37428 (-14)418 (+18)A = -32NOECCD434 (-5)423 (+21)408 (-3)428 (+25)418 (-25)A = +50a430 (+63)414 (-55)A = +118
a430 (-82)415 (+46)A = -128c429 (+154)422 (-94)A = +248b432 (+52)420 (-39)A = +91a++Zn-C3F7-Tz! nm, ("#)Entry12345678OHHHNH2EtHOHHHNH2HCH2CyNH2H3CHOHPhHNH2CH3HOHPhHOHNH2NHCH3HCH3OHPhHOHPhHNH2PhHN(CH3)2H3CHOHPhHOHHNH2HII.32II.33II.34II.35II.36II.37II.38II.39R#9:;<&'(()=+'
&?--/)7%*=%',(%ABB1%;/'/%=*)%/-.2*%/0+*,*0:"%%\00%-(/:?)(-(2':$%,(>/2(:F%%
L%5BF%Q>#L
"+%^%'4((9()F%#%(a?.D/0(2'%:?P:')/'("%/$%KL%(a?.D/0(2':%/-.2*%/0+*,*0"%P$%UY%
(a?.D/0(2':%:?P:')/'("%+$%#YLL%(a?.D/0(2':%/-.2*%/0+*,*0"P.2;.2G%+*2:'/2'%/'%Y>#L
*%^%/2;%P.2;.2G%
/H2.'7%=*)%
[2O85E5O84((9()%4/:%0/)G()%/'%Y>#L
+%^"%%
&?)6).:.2G07F%',(%[2OB
#E-O84((9()%(>,.P.'(;%',(%0/)G(:'%P.2;.2G%+*2:'/2'"%%8,.:%4/:%2*'%
(>6(+'(;%/:%',(%A0123%(2()G7%*=%',(%[2OB#E-O84((9()%4/:%,.G,(:'%*=%',(%',)((%'4((9():"%Z(>'%/%:().(:%*=%+,.)/0%/-.2*%/0+*,*0:%4()(%:?Pb(+'(;%'*%+*-60(>/3*2%4.',%/00%',)((%
'4((9():%/2;%P*',%ABB1%/2;%]rOr.:%3')/3*2:%4()(%+*2;?+'(;"%%8,(%)(:?0':%/)(%:?--/).9(;%.2%
8/P0(%!!"X"%%8,(%(>6(+'(;%ABB1%:.G2:%/)(%;('()-.2(;%?:.2G%',(%6)(D.*?:07%(:'/P0.:,(;%-2(-*2.+%

/2;%/)(%.2;.+/'(;%P7%',(%6*:.3D(%*)%2(G/3D(%:.G2"
!,%%8,(%Z(4-/2%6)*b(+3*2%.:%6)*D.;(;%/:%
)/3*2/0.9/3*2%=*)%',(%*P:()D(;%:.G2"%%E*)%',(:(%:?P:')/'(:F%[2O85E5O84((9()%4/:%',(%-*:'%
+*2:.:'(2'F%6)*D.;.2G%/2%ABB1%:.G2/0%*=%',(%(>6(+'(;%:.G2%=*)%(D()7%:?P:')/'(%'(:'(;"%%8,(%
)(:?0':%4.',%[2O855O84((9()%4()(%/%P.'%:?)6).:.2G%/:F%',(%0.'()/'?)(%)(6*)'(;%6)*'*+*0%=*)%ABB1%

/2/07:.:%*=%/-.2*%/0+*,*0:%4.',%[2O855O84((9()%)(a?.)(:%;().D/39/3*2%*=%',(%,7;)*>70%
=?2+3*2/0.'7%6).*)%'*%ABB1%3')/3*2"
*%%_?'F%=*)%-/27%:?P:')/'(:%/%)*P?:'%:.G2/0%4/:%*P:()D(;"%%
N*4(D()F%=*)%',(%@#
"FQ.CO2*)(6,(;).2(%/%+*-60(>%ABB1%:.G2/0%4/:%*P:()D(;%/2;%',(%+*-60(>%

4.',%@#
"FQ.CO!O-(',70(6,(;).2(%6)*D.;(;%/%:.G2/0%*=%',(%*66*:.'(%:.G2%6)(;.+'(;%P7%',(%
-2(-*2.+"%%8,()(=*)(F%[2O855O84((9()%4*?0;%2*'%P(%)(0./P0(%=*)%',(%/::.G2-(2'%*=%

+*2VG?)/3*2%*=%=)((%/-.2*%/0+*,*0:"%8,(%[2OB
#E-O84((9()%.:%',(%0(/:'%:?++(::=?0%*=%',(%',)((%'4((9():%'(:'(;%=*)%',(%/2/07:.:%
*=%',(%/-.2*%/0+*,*0%:?P:')/'(:"%%\:%*P:()D(;%4.',%',(%;./-.2(:F%',(%ABB1%/-60.'?;(:%*=%',(%

[2OB#E-O84((9()%+*-60(>(:%4()(%:-/00()%',/2%',(%:.G2/0:%*P:()D(;%4.',%',(%*',()%'4*%
'4((9():"%%E?)',()-*)(F%,/0=%*=%',(%:?P:')/'(:%=/.0(;%'*%=*00*4%',(%(:'/P0.:,(;%-2(-*2.+"%%8,(%

2*)(6,(;).2(:%:,*4(;%ABB1%:.G2/0:%4.',%*66*:.'(%:.G2:%/:%6)(;.+'(;%P7%',(%-2(-*2.+%/2;%',(%
RQ-*)(%:'().+/007%;(-/2;.2G%:?:P')/'(:F%@#
.FQ"CO@wCOQO/-.2*O#FQO;.6,(270(',/2*0%
/2;%@#
"FQ.CO!O-(',70(6,(;).2(F%6)*D.;(;%2*%ABB1%:.G2/0%/2;%/%+*-60(>%:.G2/0F%)(:6(+3D(07"%%
Tweezer
Ka (M-1)Error4.7x1040.998930.996280.98733Zn-C3F7Zn-TPFPZn-TPP2.7x1052.1x1056.2x1031.7x1044.6x103Binding Constants for(R,R)-pseudoephedrineOHNHR20!0.05!0.1!0.15!0.2!0.25!0.3!0.35!0.4!0.45!370!390!410!430!450!Absorbance!Wavelength (nm)
!420 nm500 equiv411 
nm3 equiv409 nmbackgroundR`!"#$%&'(()*/+
%]rOr.:%3')/3*2%*=%
[2OB#E-O84((9()%4.',%@
"COQO/-.2*P?'/2*0"%%Z*'(%',/'%
',()(%.:%/2%.2.3/0%&*)('%P/2;%:,.c%'*%K##%2-%4.',%0*4%(a?.D/0(2':%*=%/-.2*%/0+*,*0"%%8,(%
&*)('%P/2;%-*D(:%'*%KQL%2-%4.',%(>+(::%/-.2("%%&6(+')/%)(+*);(;%.2%,(>/2(:%/'%)**-%
'(-6()/'?)("9:;<&'(()*?+'
_.2;.2G%+*2:'/2':%=*)%@#"FQ"CO6:?(;*(6,(;).2(%4.',%',(%'4((9():"%8,(%]r%3')/3*2:%*=%@#
"FQ"CO6:?(;*(6,(;).2(%4.',%',(%',)((%'4((9():%.2;.+/'(%',/'%',(%
P.2;.2G%+*2:'/2'%=*)%4.',%[2OB
#E-O84((9()%/2;%[2O85E5O84((9()%/)(%:.-.0/)%P?'%[2O855O
84((9()%.:%/66)*>.-/'(07%#L%=*0;%:-/00()%@8/P0(%!!"#LC"%%E*)%/00%',)((%'4((9():F%',(%/-.2(%
P.2;.2G%.:%+*2:.;()/P07%:')*2G()%',/2%',(%,7;)*>70%',?:F%4.',%/2%(>+(::%*=%/-.2*%/0+*,*0%
6)(:(2'%',(%#$#%:?P:')/'(O'4((9()%+*-60(>%4*?0;%P)(/<%/6/)'%.2'*%/%Q$#%:?P:')/'(O'4((9()%

+*-60(>%)(:?032G%.2%/%:(+*2;%)(;%:,.c%*=%',(%&*)('%P/2;%*=%',(%'4((9()"%%E.G?)(%!!"#Q%:,*4:%',(%
]rOr.:%3')/3*2%*=%[2OB
#E-O84((9()%4.',%@
"COQO/-.2*P?'/2*0"%%8,(%6*)6,7).2%T
%&'%.:%*P:()D(;%
/'%KLX%2-"%%8,()(%.:%/2%.2.3/0%:,.c%'*%K##%2-%/'%'4*%(a?.D/0(2':%*=%/-.2*%/0+*,*0%/2;%4.',%

/;;.3*2/0%/-.2*%/0+*,*0%',(%&*)('%P/2;%:,.c:%'*%/2%(2;%6*.2'%*=%KQL%2-"%%8,(%V2/0%/P:*)P/2+(%
.:%',(%:/-(%/:%',(%T
%&'%*=%',(%[2OB
#E-O84((9()%4.',%
)(0
OP?'70/-.2(%4,.+,%.2;.+/'(:%',(%Q$#%
+*-60(>%,/:%=*)-(;%@E.G?)(%!!"XC"%%8,(%]rOr.:%&*)('%:,.c:%+*))(:6*2;.2G%'*%',(%=*)-/3*2%*=%',(%
Q$#%4/:%/0:*%*P:()D(;%=*)%[2O85E5O84((9()%.2%',.:%:'?;7%/2;%.2%',(%:(-.2/0%[2O85E5O84((9()%
)(6*)'"!,%E.2/007F%',(%[2OB
#E-O84((9()%/2;%',(%[2O85E5O84((9()%4()(%?:(;%'*%(D/0?/'(%/%:().(:%*=%
+,.)/0%;.*0:%@8/P0(%!!"##C"%%8,(%[2O855O84((9()%4/:%*-.i(;%=*)%',(%;.*0%:'?;7"%%\:%;(:+).P(;%
6)(D.*?:07F%',(%[2O85E5O84((9()%4/:%;(:.G2(;%=*)%ABB1%/2/07:.:%*=%;.*0:%;?(%'*%',(%0/+<%*=%
:?++(::%4.',%[2O855O84((9()"
!,%%\G/.2F%',(%*P:()D(;%ABB1%:.G2/0:%4.',%[2OB
#E-O84((9()%4()(%
*=%:-/00()%/-60.'?;(:%',/2%',*:(%*P:()D(;%4.',%[2O85E5O84((9()"%%!2%G(2()/0F%',(%[2OB
#E-O84((9()%;.;%2*'%6)*D.;(%)(0./P0(%)(:?0':"%%E*)%=*?)%*=%',(%:.>%;.*0%+*-60(>(:%4.',%[2OB
`EUO84((9()F%',(%ABB1%:.G2/0%4/:%+*-60(>F%?2*P:()D/P0(%*)%*=%',(%4)*2G%:.G2"%%&?)6).:.2G07F%',(%
@Q.FK.CO6(2'/2(%;.*0%G/D(%/2%ABB1%:.G2/0%*=%',(%+*))(+'%:.G2%4,()(/:F%[2O85E5O84((9()%;*(:%
2*'"%%8,(%]rOr.:%3')/3*2:%*=%',(%;.*0:%;.;%)(D(/0%',/'%',(%P.2;.2G%+*2:'/2'%=*)%',(%;.*0:%/)(%D()7%
RK:.-.0/)%=*)%[2OB
#E-O84((9()%/2;%[2O85E5O84((9()"%%8,
(%P.2;.2G%+*2:'/2'%=*)%',(%@#
"F#Q"CO'(')/;(+/2(%;.*0%4.',%P*',%'4((9():%4/:%/66)*>.-/'(07%Q>#L*%^"%8,(:(%)(:?0':%.2;.+/'(F%/:%,76*',(:.9(;F%',/'%',(%[2OB
#E-O84((9()%.:%2*'%)(0./P0(%=*)%
ABB1%(D/0?/3*2%*=%+,.)/0%:?P:')/'(:"%%8,()(%/)(%,*4(D()F%:(D()/0%6*::.P0(%(>60/2/3*2:%=*)%',(%
 Chiral DiolOHOHOH+-OHOH++426 (-13)419 (+180)410 (-31)419 (-14)405 (+8)A = -22420 (+95)410 (-39)A = +134423 (+222)411 
(-178)A = +400423 (+188)413 (-105)A = +293429 (-165)423 (+586)412 (-123)432 (-7)419 (+32)408 (-5)a424 (+124)412 (-68)A = +192Expected SignOHOHOHOH+-OH4OHOH9NO ECCD421 (+33)411 
(-19)A =  +52421 (-38)410 (+31)A = -69Zn-TPFP-Tz! nm, ("#)418 (-8)408 (+7)A = -15bZn-C3F7-Tz! nm, ("#)Entry123456OHHCH3OHHOHH3CHOHHOHHCH3OHHPhII.40II.41II.42II.43II.44II.45RY9:;<&'(()**+'
&?--/)7%*=%',(%ABB1%;/'/%=*)%;.*0:"%%\00%-(/:?)(-(2':$%,(>/2(:F%L%
5BF%
Q>#L"+%^%'4((9()F%KL%(a?.D/0(2':%;.*0"%/$%QL%(a?.D/0(2':%;.*0"%P$%eL%(a?.D/0(2':%;.*0"
4(/<()%ABB1%:.G2/0:%*P:()D(;%4.',%',(%[2OB
#E-O84((9()%+*-60(>(:%2/-(07F%4(/<()%P.2;.2G%
+*2:'/2':%;?(%'*%',(%,.G,()%M]^S%(2()G7%*=%',(%9.2+%+*)(%*=%',(%6*)6,7).2F%:-/00()%(>32+3*2%
+*(H+.(2'%*=%',(%6*)6,7).2%/2;%)(;?+(;%:'().+%;.:+).-.2/3*2"%%E.):'F%',(%:-/00()%:.G2/0:%+*?0;%
P(%/%)(:?0'%*=%4(/<()%P.2;.2G%+*2:'/2':"%%d(/<()%P.2;.2G%+*2:'/2':%)(:?0'%.2%4(/<()%:?P:')/'(O

'4((9()%+*-60(>(:%',/'%+*?0;%/++(::%/%G)(/'()%2?-P()%*=%ABB1%/+3D(%+*-60(>(:"%%8,.:%4*?0;%
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,==,<;13%(,.M*-+'L,.<%'./%'%=,<;LK3%<;*.%9,-C/%A3%3I=3(13/"%%623%'-12,+<%3I'E;.3%MK3%/;,C<%
#>@9;12%12;<%E312,/,C,*B%'./%0,-./%123%,A<3+K3/%
FGGH%<;*.'C<%E'1(2%123%<;*.%=+3/;(13/%AB%123;+%
E.3E,.;("%%O,93K3+D%123%<13+3,(23E;<1+B%,0%123%/;,C%9'<%=+,AC3E'L("%%8,+%'(B(C;(%<B<13E<D%'.%
'()%(,.M*-+'L,.%*'K3%123%A3<1%+3<-C1<%'./%123%
0#(%(B(C;(%/;,C<%9,+)3/%93CC%2,93K3+D%
0#(%'(B(C;(%'./%
'()%(B(C;(%/;,C<%9,-C/%.,1%*3.3+'13%FGGH"%%RC<,D%123%E312,/,C,*B%(,-C/%.,1%A3%
3I13./3/%1,%;.(C-/3%/;,C<%<3='+'13/%AB%E,+3%12'.%0,-+%('+A,.<"
%R%E312,/,C,*B%+3=,+13/%;.%>??d%AB%Z,C;.<);%'./%(,9,+)3+<D%/3<(+;A3/%123%
/313+E;.'L,.%,0%<13+3,(23E;<1+B%0,+%#D
(5*CB(,C%V
(%h%UD%@D%iX"
/&"/'%%623%/;,C<%93+3%M+<1%
/3+;K'L:3/%'<%123%=,+=2B+;.%A3.:,'13<D%123.%;.(,+=,+'13/%;.1,%'%C;=,<,E3"%%623%C;=,<,E3%
<3+K3<%1,%+;*;/;0B%123%W3I;AC3%/;,C%A'()A,.3%'./%'CC,9%0,+%3J(;3.1%3I(;1,.%(,-=C;.*%,0%123%
=,+=2B+;.<%'(+,<<%C,.*%/;<1'.(3"%%S;12,-1%123%C;=,<,E3D%123%/3+;K'L:3/%/;,C%;<%0+33%1,%'/,=1%'.B%

.-EA3+%,0%(,.0,+E'L,.<%'./%'<%'%+3<-C1%FGGH%;<%.,1%,A<3+K3/"%%Rj3+%,=LE;:'L,.%,0%123%C;=;/%
OHOHOCH3OCH3OOOOPMOOHCH3CH3CH3HHHHOOHCH3CH3CH3HHHHP!(S)-2-methyl-butane-2,3-diol#>b!"#$%&'((()/+
%]-=3+(2;%'./%(,9,+)3+<%A;=23.BC%/;,I,C'.3%<B<13E%0,+%FGGH%,0%/;,C<"%%623%
3N-;C;A+;-E%A31933.%123%
.%'./%
/%A;=23.BC%/;,I,C'.3<%0'K,+<%123%(,.0,+E'L,.%9;12%123%
C3'<1%<13+;(%;.13+'(L,."%%8,+%V
-X5>5E312BCA-1'.35>Da5/;,C%123%3N-;C;A+;-E%0'K,+<%
/%'./%'%
.3*'LK3%FGGH%<;*.'C%;<%,A<3+K3/"#(C3.*12D%FGGH%,0%'%K'+;31B%,0%#D
(5*CB(,C<%
V(%h%UD%@D%iX%93+3%+3(,+/3/"%%623%'-12,+<%/313+E;.3/%
12'1%/;,C<%A3'+;.*%'.%V
,D,X%(,.M*-+'L,.%*'K3%'%=,<;LK3%FGGH%<;*.'C%'./%V
-D-X%/;,C<%*3.3+'13/%'%
.3*'LK3%<;*.'C"%%
/!0&
%#DU5%'./%#Di5%/;,C<%93+3%<-AY3(13/%1,%123%FGGH%(,./;L,.<%A-1%,.CB%
A'<3C;.3%<;*.'C%9'<%,A<3+K3/"%%RC<,D%#D@5%'./%#Di5%/;,C<%*'K3%123%E,<1%;.13.<3%<;*.'C<%923+3'<%
#DU5/;,C<%=+,/-(3/%E,/3+'13%FGGH%A-1%/;,C<%,0%,123+%C3.*12<%93+3%.,1%3I'E;.3/"%%623+30,+3D%'%
*3.3+'C%FGGH%=+,1,(,C%0,+%#D(5*CB(,C<%9'<%<LCC%-.).,9."
%RC12,-*2%=+,*+3<<%2'/%A33.%E'/3%1,9'+/%3J(;3.1%E3'.<%,0%/313+E;.;.*%123%'A<,C-13%
(,.M*-+'L,.%,0%#D
(5*CB(,C<D%'%*3.3+'C%'./%+,A-<1%E312,/,C,*B%9'<%<LCC%/3<;+3/"%%8,CC,9;.*%123%
(,E=C3L,.%,0%123%K;(;.'C%/;,C%<1-/BD%H+"%Q;%3.K;<;,.3/%3I13./;.*%123%4.5678756933:3+%FGGH%
E312,/,C,*B%1,%;.(C-/3%#D
(5*CB(,C<"%%623%*CB(,C<%93+3%<B.123<;:3/%AB%3=,I;/'L,.%,0%123%
(,++3<=,./;.*%/;3.3%0,CC,93/%AB%k'(,A<3.l<%O\_%1,%=+,K;/3%123%(2;+'C%3=,I;/3<"
/(%&0%%623<3%
3=,I;/3<%93+3%<-AY3(13/%1,%QRO%+;.*%,=3.;.*%1,%*3.3+'13%123%(2;+'C%*CB(,C<"%%623<3%*CB(,C<%93+3%
OHOHporphyrin esterlipid (DPC)RRRRRRliposomes15#>i!"#$%&'((()0+
%FGGH%=+,1,(,C%0,+%#D
(5*CB(,C<%V.%h%UD%@D%iX%/3<(+;A3/%AB%Z,C;.<);%'./%
(,9,+)3+<"%%623%/;,C%;<%M+<1%/3+;K'L:3/%AB%'%=,+=2B+;.%A3.:BC%3<13+%123.%123%/3+;K'L:3/%
/;,C%;<%;.(,+=,+'13/%;.%'%C;=,<,E3%,0%
/;<13'+,BC5<.5*CB(3+,5a5=2,<=2'L/BC(2,C;.3%VH7GX"%%
H;,C<%,0%V,D,X%(,.M*-+'L,.%*'K3%'%=,<;LK3%FGGH%<;*.'C"/&"/'123.%<-AE;m3/%1,%FGGH%'.'CB<;<%9;12%4.5678756933:3+
%VGU54.5678756933:3+XD%123%+3<-C1<%,0%
92;(2%'+3%<-EE'+;:3/%;.%8;*-+3%!!!"@"%%[0%123%193CK3%V
,D,X%*CB(,C<D%13.%=+,K;/3/%'.%FGGH%<;*.'C%
9;12%'%=,<;LK3%<;*."
&!%%!1%9'<%+3'<,.3/%12'1%123%V
,D,X%(,.M*-+'L,.%;./-(3<%'%(C,()9;<3%23C;(;1B%
;.1,%123%=,+=2B+;.%1933:3+%123+30,+3D%'CC%,0%123%V
,D,X%<-A<1+'13<%<2,-C/%*3.3+'13%'%=,<;LK3%
FGGH%'./%123%V
-D-X%<-A<1+'13%<2,-C/%=+,K;/3%'%.3*'LK3%FGGH%<;*.'C"%%623+3%93+3%2,93K3+%12+33%
+3<-C1<%12'1%/;/%.,1%M1%9;12%123%*3.3+'C%1+3./"%%8;+<1D%V>
-Dd-X5=3.1'.35>Dd5/;,C%V#Da5/;,CX%9'<%
1,41,51,61,72OHOH1,3aOHOHOHOH3OHOH4OHOH424 (+205) 413 (-163)A= +368424 (+174)  413 (-135)A = +309426 (-70)  416 (+53)A = -123422 (-237)  416 (+199)A = +436424 (+81) 419 (-71) A = +1525OHOH6OHOH7OHOH9OHOH1,81,91,121,10426 (+146) 415 (- 140) A = +286423 (+172) 414 (-130)A = +302425 (+314) 415 (-177)A = +491430 (-91)  423 (+ 506)414 (-171)OHOH1,2425 (+128) 413 (-96) A = +22413OHOH7BnOHBnOH9BnOHOH1,16b1,11
1,10422 (+28) 415 (-20)A = +58423 (-163) 416 (+143)A = -306422 (-38)  415 (+42)A = -80#a?!"#$%&'((()1+
%623%FGGH%+3<-C1<%0,+%123%#D
(5*CB(,C<%9;12%GU54.5678756933:3+"%%623%*CB(,C<%
2;*2C;*213/%;.%AC-3%*3.3+'13/%FGGH%+3<=,.<3<%12'1%/;/%.,1%E'1(2%123%*3.3+'C%1+3./%0,+%
123%<3+;3<"%%RCC%E3'<-+3E3.1<$%?%
1GD%23I'.3<D%d?%3N-;K'C3.1<%*CB(,C"%'$%#??%3N-;K'C3.1<%
*CB(,C"%A$%U%
1GD%#??%3N-;K'C3.1<%*CB(,CD%Un%GO
#GC#e23I'.3<"&!3I=3(13/%1,%*;K3%'%.3*'LK3%<;*.'C%'./%V>
,D@,X5,(1'.35>D@5/;,C%V#Dc%/;,CX%<2,-C/%2'K3%=+,/-(3/%'%
=,<;LK3%<;*.%2,93K3+D%A,12%*BC(,C<%*3.3+'13/%FGGH%<;*.'C<%,0%123%,==,<;13%<;*."%%RC<,D%V>
,D%#a,X5131+'/3('.35>D#a5/;,C%V#D#>5/;,CX%=+,K;/3/%'%(,E=C3I%1+;<;*.'13%FGGH%(-+K3"
%623<3%+3<-C1<%;./;('13/%12'1%+353.*;.33+;.*%,0%123%1933:3+%9'<%+3N-;+3/"%%623%=,+=2B+;.%

2'/%A33.%,=LE;:3/%1,%3.2'.(3%123%Q39;<%'(;/;1B%,0%123%:;.(%'./%=+,E,13%A;./;.*%,0%,IB*3.%
0-.(L,.'C;L3<%123+30,+3D%123%=,+=2B+;.%-.;1%9'<%1,%+3E';.%'<%123%1+;<V=3.1'W-,+,=23.BCX%
=,+=2B+;."%%623+30,+3D%,123+%K'+;'AC3<%,0%123%=,+=2B+;.%1933:3+%2'/%1,%A3%(,.<;/3+3/"%%R%<1-/B%

(,./-(13/%H+"%Z'+;.'%6'.'<,K'%<2,93/%12'1%<2,+13.;.*%123%C;.)3+%A31933.%123%=,+=2B+;.%-.;1<%
3.2'.(3/%FGGH%<;*.'C<%0,+%3K'C-'L,.%,0%(2;+'C%/;'E;.3<%'./%('+A,IBC;(%'(;/<%9;12%4.56775
6933:3+"&%%&B%(2'.*;.*%123%C;.)3+%0+,E%'%MK3%E312BC3.3%-.;1%VGU54.567756933:3+X%1,%'%12+33%
E312BC3.3%-.;1%VGa54.567756933:3+XD%123%FGGH%<;*.'C<%93+3%<1+,.*3+%0,+%E,<1%,0%123%<-A<1+'13<%
3K'C-'13/"%%]3C3(13/%+3<-C1<%9;12%(2;+'C%/;'E;.3<%'+3%<-EE'+;:3/%;.%8;*-+3%!!!"b"%%!1%9'<%+3'<,.3/%
NNNNPhPhPhOONNNNPhPhPhOOn n = 1, C3-Zn-TPP-Tweezer
 n = 3, C5-Zn-TPP-Tweezer
ZnZnH2NNH2CH3H2NNH2CONH2H2NCO2CH3NH2C5-Tweezer 
  A = -160C3-Tweezer 
  A = -275C5-Tweezer 
  A = -36C3-Tweezer 
  A = -156C5-Tweezer 
  A = -392C3-Tweezer 
  A = -400#a#!"#$%&'((()2+
%]-EE'+B%,0%FGGH%+3<-C1<%,0%123%4.567756933:3+<%'./%/;'E;.3<"%%!.%*3.3+'CD%
123%'E=C;1-/3<%'+3%C'+*3+%9;12%123%Ga54.567756933:3+%/-3%1,%123%<2,+13+%C;.)3+"'(12'1%AB%<2,+13.;.*%123%C;.)3+%C3.*12D%123%1933:3+
%2'/%0393+%/3*+33<%,0%0+33/,E"%%8-+123+E,+3D%
123%A;./;.*%=,()31%A31933.%123%19,%=,+=2B+;.<%;<%<E'CC3+%0,+%123%1933:3+%9;12%123%<2,+13+%
C;.)3+"%%623+30,+3D%123%<-A<1+'1351933:3+%(,E=C3I%9;12%123%Ga54.567756933:3+%9,-C/%2'K3%
0393+%/3*+33<%,0%0+33/,ED%<2,-C/%A3%E,+3%+;*;/%/-3%1,%123%<E'CC3+%A;./;.*%=,()31%'./%9,-C/%

0'K,+%'%<;.*C3%FGGH%'(LK3%(,.0,+E'L,."%%62;<%9,-C/%123.%C3'/%1,%E,+3%+,A-<1%FGGH%<;*.'C<"%%
S;12%123%+3<-C1<%,0%12;<%<1-/B%;.%E;./D%'%<3+;3<%,0%4.5678756933:3+<%93+3%3.K;<;,.3/%1,%K'+B%123%
<;:3%,0%123%A;./;.*%=,()31%,0%123%1933:3+"!!!"a$%H3<;*.%'./%]B.123<;<%,0%4.5678756933:3+<%9;12%`'+;3/%Q;.)3+%Q3.*12<%623%/+;K3%0,+%(2'.*;.*%123%C;.)3+%C3.*12%9'<%;.;L'13/%AB%123%=+,=,<3/%E,/3%,0%A;./;.*%

0,+%'%*;K3.%<-A<1+'13%9;12%'%=,+=2B+;.%1933:3+"%%!1%9'<%2B=,123<;:3/%12'1%123+3%93+3%19,%9'B<%
;.%92;(2%123%*CB(,C%(,-C/%M1%;.%123%A;./;.*%=,()31%,0%4.5678756933:3+%VGU54.5678756933:3+XD%
3;123+%123%=,+=2B+;.<%'+3%0,+(3/%'='+1%V8;*-+3%!!!"i%RX%,+%123%*CB(,C%0,C/<%;.1,%'%2;*2%3.3+*B%

(,.0,+E'L,.%1,%M1%;.%123%=,()31%V8;*-+3%!!!"i%&X"%%8;+<1D%A;./;.*%,0%123%<-A<1+'13%(,-C/%0,+(3%123%
=,+=2B+;.<%'='+1"%%623%=,+=2B+;.<%'+3%12,-*21%1,%A3%(,50'(;'C%923.%123%<-A<1+'13%;<%A,-./"%%R<%
123%*CB(,C%A3(,E3<%C,.*3+D%123%=,+=2B+;.<%9,-C/%A3%=-<23/%0'+123+%'='+1%<-(2%12'1%123%

=,+=2B+;.<%+3E';.%(,50'(;'C%A-1%123%'.*C3%'./%/;<1'.(3%A31933.%123E%;.(+3'<3<"%%!1%;<%A3C;3K3/%
12'1%'1%<,E3%=,;.1%123%C;.)3+%A31933.%123%=,+=2B+;.<%;<%1,,%<2,+1%'./%123%=,+=2B+;.<%('.%.,1%
<3='+'13%3.,-*2%1,%'((,EE,/'13%123%C3.*12%,0%123%*CB(,C"%%RC13+.'LK3CBD%;0%123%=,+=2B+;.<%'+3%

.,1%<3='+'L.*D%123%*CB(,C%(,-C/%0,C/%1,%M1%123%A;./;.*%=,()31%/3M.3/%AB%123%1933:3+"%%O,93K3+D%
123%*CB(,C%9,-C/%9+'=%;.1,%'%2;*2%3.3+*BD%.,.5C;.3'+D%(,.0,+E'L,.%1,%A;./%1,%123%1933:3+"%%623%
-.0'K,+'AC3%(,.0,+E'L,.%,0%3;123+%123%1933:3+%,+%123%*CB(,C%9,-C/%+3<-C1%;.%123%-.+3C;'AC3%
#a>FGGH%+3<-C1<"%%!0%12;<%2B=,123<;<%9'<%(,++3(1D%
123.%'%1933:3+%9;12%'%<2,+13+%C;.)3+%9,-C/%A3%C3<<%
+3C;'AC3%12'.%123%,+;*;.'C%1933:3+%'<%<2,+13.;.*%123%C;.)3+%9,-C/%0-+123+%+3/-(3%123%<;:3%,0%123%
A;./;.*%=,()31%'./%A;./;.*%,0%123%*CB(,C%9,-C/%A3%C3<<%0'K,+'AC3"%%[.%123%,123+%2'./D%'%1933:3+%
9;12%'%C,.*3+%C;.)3+%<2,-C/%2'K3%'%C'+*3+%A;./;.*%=,()31D%A3%E,+3%'((,EE,/'L.*%,0%123%C,.*%
2OHOH8OHOHHOOHHOOHA: Porphyrins Forced to Separate:B: Glycol adopts a high energy conformation:P1P2ZnZnP1P2ZnZnP1P2ZnZnHOOHOHHOP1P2ZnZnP1P2ZnZn#aa!"#$%&'((()3+
%623%=,<<;AC3%A;./;.*%E,/3<%,0%'%#D
(5*CB(,C%9;12%GU54.5678756933:3+"%%R<%123%
.-EA3+%,0%E312BC3.3<%<3='+'L.*%123%2B/+,IBC<%;.(+3'<3<D%3;123+%123%=,+=2B+;.<%'+3%
0,+(3/%0'+123+%'='+1%V
4X%,+%123%*CB(,C%E-<1%9+'=%;.1,%'%2;*2%3.3+*B%(,.0,+E'L,.%V
5X"%%
623%-.0'K,+'AC3%(,.0,+E'L,.%,0%3;123+%123%1933:3+%,+%123%*CB(,C%(,-C/%A3%('-<;.*%123%
FGGH%+3<-C1<%12'1%/,%.,1%M1%123%E.3E,.;("(2';.%*CB(,C<%'./%123%FGGH%+3<-C1<%<2,-C/%A3%E,+3%+3C;'AC3"%%623%=C'.%0,+%.39%1933:3+<%9'<%0,+%
123E%1,%2'K3%C;.)3+<%0+,E%12+33%E312BC3.3%-.;1<%1,%.;.3%E312BC3.3%-.;1<%V;.(C-/;.*%MK3%
E312BC3.3%C;.)3+%,0%123%,+;*;.'C%1933:3+D%GU54.5678756933:3+X"
%623%<B.123<;<%,0%123%6787%6933:3+<%0,CC,93/%123%C;13+'1-+3%+3=,+13/%=+,(3/-+3%0,+%GU5

4.5678756933:3+%V](23E3%!!!"#X"
(%%623%6787%E312BC%3<13+%V
*X%9'<%,A1';.3/%0+,E%'.%'(;/%
('1'CB:3/%(,./3.<'L,.%,0%=3.1'W-,+,A3.:'C/32B/3D%=B++,C3%'./%d50,+EBCE312BCA3.:,'13%;.%
0';+CB%*,,/%B;3C/%0,+%'%=,+=2B+;.%(,./3.<'L,.%V#@n%B;3C/X"%%OB/+,CB<;<%,0%123%3<13+%-./3+%A'<;(%
(,./;L,.<%=+,K;/3/%123%6787%'(;/%V
,X%;.%N-'.L1'LK3%B;3C/"%%623%FHG%E3/;'13/%(,-=C;.*%,0%123%

6787%R(;/%V
,X%9;12%123%'==+,=+;'13%13+E;.'C%/;,C%=+,K;/3/%123%Gd%'./%Gc5Gi%E,.,C;.)3+<%V
-61X%'./%<-A<3N-3.1%FHG%(,-=C;.*%,0%123%Gd5Gi%E,.,C;.)3+<%9;12%123%6787%'(;/%B;3C/3/%123%Gd%'./%
Gc5Gi%0+33%1933:3+<%V
26*,X"%%623%B;3C/<%0,+%123%<3(,./%FHG%(,-=C;.*%93+3%0';+CB%C,9"%%62;<%9'<%

3I=3(13/%'<%123%;.;L'C%(,-=C;.*<%1,%123%E,.,C;.)3+<%*'K3%E,/3+'13%B;3C/<"%%6B=;('CCBD%123%<3(,./%
(,-=C;.*%2'<%C,93+%B;3C/<%12'.%123%M+<1%(,-=C;.*"%%4;.('L,.%,0%123%0+33%1933:3+<%9;12%:;.(%!!%
'(31'13%*3.3+'13/%123%VGd%'./%Gc5GiX54.5678756933:3+<%V
*-6*1X%;.%+'123+%C,9%B;3C/<%0,+%<,E3%

('<3<"%%62;<%;<%C;)3CB%/-3%1,%123%*3.3+'L,.%,0%'(3L(%'(;/%-=,.%:;.('L,.%,0%123%1933:3+%'<%'(;/%;<%
).,9.%1,%('-<3%/3E31'CC'L,.%,0%E31'CC,=,+2B+;.<"%%];E-C1'.3,-<CBD%H+"%Q;%<B.123<;:3/%123%Ga5
4.5678756933:3+%0,CC,9;.*%123%<'E3%=+,(3/-+3%9;12%#Da5=+,='.3%/;,C"%%623<3%1933:3+<%93+3%

123.%-<3/%0,+%FGGH%'.'CB<;<%,0%123%#D(5*CB(,C<"
#adOHFFFFFOHOONH(3 equiv)NNHNHNC6F5C6F5C6F5OO1. BF3OEt2 (0.8 equiv)    CH2Cl2, N2, rt, 2 h2. p-chloranil (8 equiv)    CH2Cl2, N2, rt, 2 h    17%2 M NaOHTHF, 
reflux, 10 hquantitativeROOHROOOHHOOHDMAP 
(1.3 equiv) EDC (1.3 equiv)CH2Cl2, N2, rt, 24 hROOROOZn(OAc)2 (excess)CH2Cl2, N2 rt, 40 hIII.1TPFP 
Methyl Ester(1 equiv)(4 equiv)III.2TPFP 
Acid(1.3 equiv)DMAP 
(1.3 equiv) EDC (1.3 equiv)CH2Cl2, N2, rt, 24 hIII.2(1.3 equiv)nIII.3, n = 1, C4-TPFP 
Monolinker, 
36%III.4, n = 3, C6-TPFP 
Monolinker, 
52%III.5, n = 4, C7-TPFP 
Monolinker, 
59%III.6, n = 5, C8-TPFP 
Monolinker, 
74%III.7, n = 6, C9-TPFP 
Monolinker, 
47%nIII.8,   n = 1, C4-TPFP 
Free Tweezer, 
45%III.9,   n = 3, C6-TPFP 
Free Tweezer, 
24%III.10, n = 4, C7-TPFP 
Free Tweezer, 
30%III.11
, n = 5, C8-TPFP 
Free Tweezer, 
35%III.12, n = 6, C9-TPFP 
Free Tweezer, 
28%NNNNC6F5C6F5C6F5OONNNNC6F5C6F5C6F5OOnIII.13, n = 1, C4-Zn-TPFP-Tweezer, 
21%III.14, n = 3, C6-Zn-TPFP-Tweezer, 
74%III.15, n = 4, C7-Zn-TPFP-Tweezer, 
63%III.16, n = 5, C8-Zn-TPFP-Tweezer, 
50%III.17, n = 6, C9-Zn-TPFP-Tweezer, 
20%ZnZnnR =#aU789&:&'((()*+'
]B.123<;<%,0%123%Gd%'./%Gc5Gi54.5678756933:3+<"!!!"d$%FGGH%]1-/B%,0%123%#D(5fCB(,C<%T<;.*%123%Z,/;M3/%4.5678756933:3+<%8,+%123%FGGH%<1-/BD%3'(2%L1+'L,.%9'<%(,./-(13/%;.%23I'.3<%'1%?%
1G%9;12%>%oZ%'./%
K'+;3/%3N-;K'C3.1<%,0%123%*CB(,C"%%]-EE'+;:3/%;.%123%0,CC,9;.*%1'AC3<%V6'AC3%!!!"#e>X%'+3%123%
+3<-C1<%0,+%123%<1-/B"%%623%FGGH%+3<-C1<%12'1%/,%.,1%E'1(2%123%E.3E,.;(%'+3%2;*2C;*213/%;.%+3/"%%
!.13+3<L.*CBD%123%,.CB%1933:3+%,0%123%<3+;3<%12'1%=+,K;/3/%123%3I=3(13/%FGGH%+3<-C1%0,+%3K3+B%

*CB(,C%13<13/%9'<%Ga54.5678756933:3+%123+30,+3D%<2,+13.;.*%,0%123%C;.)3+%C3'/<%1,%E,+3%<1'AC3%
(,E=C3I3<%0,+%'CC%,0%123%C,.*%(2';.%*CB(,C<"%%623%Ga54.5678756933:3+%9'<%+3=,+13/%'<%123%
,=LE'C%1933:3+%0,+%'.%FGGH%=+,1,(,C%,0%#D
(5*CB(,C<%'./%'%E.3E,.;(%9'<%3<1'AC;<23/%0,+%#D
(5*CB(,C<%-<;.*%12;<%1933:3+"
&!%%623%E.3E,.;(%'./%'%.39%C;.3%,0%+3'<,.;.*%1,%3I=C';.%123%<-((3<<%
,0%12;<%1933:3+%9;CC%A3%/;<(-<<3/%;.%/-3%(,-+<3"%%623%FGGH%+3<-C1<%0,+%123%C,.*3+%C;.)3+%1933:3+<%
/;/%.,1%<-==,+1%,-+%,+;*;.'C%2B=,123<;<%2,93K3+D%123+3%93+3%<,E3%;.13+3<L.*%+3<-C1<%'./%
,A<3+K'L,.<%E'/3%/-+;.*%123%(,-+<3%,0%123%<1-/B"%%G,-.13+;.1-;LK3CB$p123%<2,+1%(2';.%*CB(,C<%93+3%123%E,<1%=+,AC3E'L(%p123%C,.*%(2';.%*CB(,C<%(,.<;<13.1CB%*3.3+'13/%FGGH%<;*.'C<%,0%123%(,++3(1%<;*."%%p\-<%0,+%123%C,.*%*CB(,C<%9;12%Ga%1933:3+%93+3%q#?2%Zp\-<%0,+%123%C,.*%(2';.%*CB(,C<%9;12%Gb%'./%Gi%1933:3+%93+3%q#?&%Z%623%<2,+13+%(2';.%*CB(,C<%V#Da%5%#DcX%93+3%123%E,<1%=+,AC3E'L(%V6'AC3%!!!"#X%0,+%'CC%123%
1933:3+<%3I(3=1%Ga54.5678756:"%%FGGH%'.'CB<;<%,0%V>
-D%d
-X5=3.1'.3%/;,C%*3.3+'13/%123%3I=3(13/%
.3*'LK3%<;*.'C%9;12%,.CB%123%Ga%'./%Gd%1933:3+<D%123%1933:3+<%9;12%123%<2,+13<1%C;.)3+<"%%
!.(+3'<;.*%123%C3.*12%,0%123%C;.)3+%E'/3%FGGH%C3<<%+3C;'AC3%0,+%123%<2,+1%(2';.%*CB(,C<%'<%
;.(,.<;<13.(;3<%93+3%,A<3+K3/%0,+%123%#Da%5%#Dc%*CB(,C<%9;12%K'+;,-<%1933:3+<"%%623<3%+3<-C1<%
<-**3<1%12'1%123%(,E=C3I3<%,0%123%1933:3+<%9;12%C,.*3+%C;.)3+<%'./%<2,+1%(2';.%*CB(,C<%'+3%C3<<%
#ac1,41,51,6429 (-21) 419 (+36) A = -57424 (+205) 413 (-163)A= +368423 (+69) 413 (-55) A = +124Tweezer
Glycol424 (+174)  413 (-135)A = +309423 (+54)  414 (-89)A = +143423 (+161) 414 (-87) A = +258428 (-18)421 (+155)  413 (-58)426 (-70)  416 (+53)A = -123425 (-148)  414 (+222)A= -370a425 (-247) 416 (+187)A = -434aNo ECCD2OHOH1,3OHOHOHOH3OHOH426 (-23) 417 (+19) A = -42424 (+81) 419 (-71) A = +152423 (+303) 414 (-203) A = +506423 (+300) 414 (-193) A = +493423 (-38) 412 (+37) A = -73424 (+72) 414 (-66) A = +138423 (+136) 414 (+100) A = +236422 (+322) 415 (-203) A = +525423 (+64) 413 (-43) A = +107424 (-50)417 (+81)A = -131422 (+87)  415 (-43)A= +130423 (+64) 416 (-37)A= +101422 (+118) 
415 (-131) A = +249423 (+286) 414 (-224) A = +510425 (+52) 414 (-48) A = +100423 (+66) 413 (-48) A = +114
b424 (-90)417 (+147)410 (-21)C3C4C5C6C7C8
C9OH1,2424 (+92) 412 (-115)
 A = +207425 (+128) 413 (-96) A = +224424 (+112) 
411 
(-75) A = +187425 (+58) 410 (-16) A = +74425 (+102) 413 (-77) A = +179424 (+25) 413 (-13) A = +38424 (+135) 412 (-76) A = +211
OH#a@;<=>&'((()*+
%]-EE'+B%,0%FGGH%+3<-C1<%0,+%123%#D>%5%#Dc5*CB(,C<%9;12%Ga%5%Gi54.567875
6933:3+<"%%_3<-C1<%;.%+3/%/,%.,1%E'1(2%123%<;*.%=+3/;(13/%AB%123%E.3E,.;("%%F'(2%3.1+B%
;.%123%1'AC3%*;K3<%123%M+<1%G,m,.%3g3(1D%r%.E%VstXD%<3(,./%G,m,.%3g3(1%r%.E%VstX%'./%
,K3+'CC%'E=C;1-/3%VRX"%%RCC%E3'<-+3E3.1<$%23I'.3<D%?%
1GD%>%oZ%1933:3+D%d?%3N-;K'C3.1<%
*CB(,C"%'$%#?%3N-;K'C3.1<%*CB(,C"%A$%>?%3N-;K'C3.1<%*CB(,C"%1,7423 (+80)  417 (-53)A = +133422 (-237)  416 (+199)A = +436422 (-236)  416 (+288)A = -524423 (+294)  414 (-262)A = +556b4OHOH423 (+152) 414 (-142) A = +294424 (+186)  415 (-126)A = +312424 (+613)  415 (-331)A = +9445OHOH6OHOH7OHOH9OHOH1,81,91,121,10425 (+129)  417 (-110)
A = +239426 (+146) 415 (- 140) A = +286422 (+161) 413 (-71) A = +232422 (+184)  416 (-193)A = +377425 (+90) 417 (-72) A = + 162423 (+172) 414 (-130)A = +302429 (+137) 409 (-80)A = + 217422 (+306)415 (-238)A = + 544425 (+142)  416 (-116)
A =  + 258425 (+314) 415 (-177)A = +491423 (+107) 415 (-99)A = + 206424 (+501)  416 (-279)A = + 780424 (+82) 415 (-51) A =  + 133430 (-91)  423 (+ 506)414 (-171)423 (+84)  417 (-57)A = + 141422 (+127) 416 (-105)A = + 232b424 (+400) 415 (-351) A = +751427 (+408) 416 (-326) A = +734424 (+193) 415 (-123) A = +316426 (+156) 416 (-197) A = +353423 (+1130) 
416 (-876) A = +2006423 (+511) 
 413 (-289)A = +800423 (+902) 416 (-781) A = +1683423 (+433)  416 (-311)
A= +744422 (+1015) 415 (-829)A= + 1844423 (+1383) 416 (-1051) A = +2434423 (+2311) 
416 (-1780) A = +4091423 (+2028) 416 (-1556) A = +3584Tweezer
GlycolC3C4C5
C6C7C8C9#ab;<=>&'(((),+
%]-EE'+B%,0%FGGH%+3<-C1<%0,+%123%#D@%5%#D#?%'./%#D#>5*CB(,C<%9;12%Ga%5%Gi54.5
678756933:3+<"%%_3<-C1<%;.%+3/%/,%.,1%E'1(2%123%<;*.%=+3/;(13/%AB%123%E.3E,.;("%%623%
+3<-C1<%9;12%3I(3=L,.'CCB%C'+*3%'E=C;1-/3<%'+3%2;*2C;*213/%;.%AC-3"%%F'(2%3.1+B%;.%123%
1'AC3%*;K3<%123%M+<1%G,m,.%3g3(1D%r%.E%VstXD%<3(,./%G,m,.%3g3(1%r%.E%VstX%'./%,K3+'CC%

'E=C;1-/3%VRX"%RCC%E3'<-+3E3.1<$%23I'.3<D%?%
1GD%>%oZ%1933:3+D%d?%3N-;K'C3.1<%*CB(,C"%'$%
#?%3N-;K'C3.1<%*CB(,C"%A$%>?%3N-;K'C3.1<%*CB(,C"%<1'AC3"%%6,%A+;.*%123%=,+=2B+;.<%;.%(C,<3%3.,-*2%=+,I;E
;1B%1,
%A;./%1,%123%2B/+,IBC%*+,-=<%,0%123%
<2,+1%(2';.%*CB(,C<D%123%E312BC3.3%(2';.%,0%123%1933:3+%;<%C;)3CB%'/,=L.*%'%2;*2%3.3+*BD%.,.5
C;.3'+%(,.0,+E'L,.%92;(2%+3<-C1<%;.%'.%-.0'K,+'AC3D%2;*2%3.3+*B%(,E=C3I%V8;*-+3%!!!"#?X"%%623<3%
2;*2%3.3+*BD%C3<<%<1'AC3%(,E=C3I3<%(,-C/%A3%'((3<<;.*%'%.-EA3+%,0%/;g3+3.1%FGGH%'(LK3%

(,E=C3I3<%C3'/;.*%1,%FGGH%<;*.'C<%,0%123%;.(,++3(1%<;*."%623%FGGH%+3<-C1<%0,+%123%(,E=C3I3<%,0%123%C,.*3+%(2';.%*CB(,C<%V#D@%5%#D#>X%9;12%'CC%,0%123%
1933:3+<%=+,K;/3/%A;<;*.'13%(-+K3<%,0%123%=+3/;(13/%<;*.D%9;12%123%3I(3=L,.%,0%19,%(,E=C3I3<D%

Gc%6933:3+%9;12%#D@5*CB(,C%'./%GU%6933:3+%9;12%#D#>5*CB(,C"%%62;<%9'<%'%<-+=+;<;.*%+3<-C1"%%
7'+L(-C'+CB%0,+%123%C,.*%(2';.%*CB(,C<%9;12%123%1933:3+<%,0%<2,+1%C;.)3+%C3.*12<"%%!.;L'CCBD%;1%9'<%
12,-*21%12'1%-=,.%A;./;.*%9;12%123%1933:3+D%123%*CB(,C<%9,-C/%A3%0,+(3/%1,%'/,=1%'%2;*2%

3.3+*BD%.,.5<1'**3+3/%(,.0,+E'L,.%123+3AB%(+3'L.*%2;*2%3.3+*BD%-.<1'AC3%(,E=C3I3<%V8;*-+3%
P1P2ZnZnOOOOHOOHP1P2ZnZnOOOOHOOHC3-Zn-TPFP-TzC8-Zn-TPFP-Tz#ai!"#$%&'((()*?+
%G,E=C3I3<%,0%'%#D>5*CB(,C%9;12%Ga5%'./%Gb54.5678756933:3+"%%!1%;<%12,-*21%
12'1%123%C;.)3+%,0%Gb54.5678756933:3+%9;CC%2'K3%1,%3.13+%'%2;*2%3.3+*B%(,.0,+E'L,.%1,%
A;./%9;12%123%*CB(,C"!!!"i%&X"%%623+30,+3D%;1%9'<%3I=3(13/%12'1%123%FGGH%'
.'CB<;<%,0%123%C,.*3+%(2';.%*CB(,C<%9;12%<2,+1%
C;.)3+%1933:3+<%9,-C/%A3%;.(,.<;<13.1"%%O,93K3+D%12;<%9'<%<2,9.%1,%A3%;.(,++3(1"
%8-+123+E,+3D%0,+%123%Gb%'./%Gi%1933:3+<D%FGGH%'.'CB<;<%,0%123%#Db%5%#D#>%*CB(,C<%+3<-C13/%
;.%<-+=+;<;.*CB%C'+*3%'E=C;1-/3<D%'1%LE3<%;.%3I(3<<%,0%#???"%%62;<%;./;('13<%12'1%123%C,.*3+%C;.)3+%%

,0%123%1933:3+%=+,E,13<%A;./;.*%9;12%123%C,.*%(2';.%*CB(,C<D%12-<%<-==,+L.*%,-+%,+;*;.'C%
2B=,123<;<%12'1%E,+3%W3I;A;C;1B%;.%123%1933:3+%9,-C/%0'K,+%(,E=C3I%0,+E'L,.%9;12%123%C,.*%
(2';.%*CB(,C<%AB%(+3'L.*%'%C'+*3+%A;./;.*%=,()31"%%O,93K3+D%123%;.(,.<;<13.(;3<%,A<3+K3/%9;12%

123%<2,+1%(2';.%*CB(,C<%3C;E;.'13<%123%Gc%5%Gi%1933:3+<%'<%+3C;'AC3%2,<1%E,C3(-C3<%0,+%123%
/313+E;.'L,.%,0%(,.M*-+'L,.%0,+%#D(5*CB(,C<"
%!.1+;*-3/%AB%123%/+'E'L(%FGGH%<;*.'C<%,0%123%Gb5%'./%Gi54.5678756933:3+<%9;12%123%#Db%

5%#D#>5*CB(,C<D%'%T`5`;<%'.'CB<;<%,0%3'(2%(,E=C3I%9'<%-./3+1')3."%%623%=-+=,<3%,0%123%T`5`;<%
'.'CB<;<%9'<%1,%3C-(;/'13%123%A;./;.*%(,.<1'.1<%0,+%3'(2%(,E=C3I%9;12%123%2B=,123<;<%12'1%123%
(,E=C3I3<%,0%Gb5%'./%Gi54.5678756933:3+<%9;12%123%#Db%5%#D#>5*CB(,C<%2'/%<;*.;M('.1CB%C'+*3+%

A;./;.*%(,.<1'.1<"%%623%C'+*3%A;./;.*%(,.<1'.1%9,-C/%;./;('13%'%L*21%'./%+;*;/%(,E=C3I%92;(2%
9,-C/%+3/-(3%123%.-EA3+%,0%FGGH%(,E=C3I3<%(,.1+;A-L.*%1,%123%,A<3+K3/%<;*.'C%'./%(,-C/%A3%
123%-./3+C;.*%('-<3%,0%123%;.13.<3%<;*.'C<"%%!.%123%0,CC,9;.*%1'AC3<D%V6'AC3%!!!"aedX%123%A;./;.*%

(,.<1'.1%/'1'%;<%<-EE'+;:3/"%%%623<3%A;./;.*%(,.<1'.1%('C(-C'L,.<%=+,K;/3/%<,E3%;.13+3<L.*%,A<3+K'L,.<"%%8;+<1CBD%123%
#D(5*CB(,C%9;12%GU5D%Gc5%,+%G@54.5678756933:3+%(,.<;<13.1CB%=+,/-(3/%A;./;.*%(,.<1'.1<%;.%123%

+'.*3%,0%#%5%UI#?
/%Z"%%62;<%K'C-3%(,++3C'13<%93CC%9;12%123%C;13+'1-+3%+3=,+13/%\
-%0,+%GU54.567875
6933:3+%9;12%'%K;(;.'C%/;,C%V#"UI#?
/%ZX"(%%O,93K3+D%,123+%1933:3+<%,0%123%<3+;3<%VGa5D%Gd5%D%Gb5%
'./%Gi5XD%<2,93/%/;g3+3.1%1+3./<"%%623%,A<3+K3/%A;./;.*%(,.<1'.1<%9;12%123<3%1933:3+<%
#d?1,41,51,6 A = -5747654 ± 21820.99942A= +368ND A = +1249312 ± 911
0.99795Tweezer
GlycolA = +30924985 ± 16090.98852A = +14353745 ± 45650.9957 A = +25834729 ± 33170.99591Trisignate
5094 ± 2070.99886A = -12312333 ± 3630.9992A= -370a20344 ± 13390.997A = -434a7783 ± 7030.99406No ECCD7144 ± 930.999792OHOH1,3OHOHOHOH3OHOH A = -4233546 ± 50140.97485 A = +15251611 
± 18500.99929 A = +5065004 ± 5280.99304 A = +49337737 ± 28040.99306 A = -7328439 ± 31420.99631 A = +138ND A = +23615678 ± 29460.99878 A = +5256410 ± 2870.99744 A = +10723175 ± 53900.99977A = -13171076 ± 120270.98957A= +13013497 ± 4940.99844A= +10112045 ± 3150.99772 A = +24997270 ± 122730.99148 A = +5108430 ± 1580.99966 A = +10015829 ± 9260.99579 A = +114
b6198 ± 4660.99299Trisignate
43065 ± 94640.96577C3C4C5C6
C7C8C9OH1,2 A = +20750603 ± 176790.93351 A = +22498587 ± 75720.99766 A = +18732189 ± 28860.99466 A = +746013 ± 9220.98012 A = +179Ka = 21020 ± 2480R2 = 0.99146 A = +3816910 ± 9270.99869 A = +211
15218 ± 10640.993OH#d#;<=>&'((()-+
%%&;./;.*%(,.<1'.1<%0,+%(,E=C3I3<%,0%123%#D>%5%#Dc%*CB(,C<%9;12%123%Ga%5%Gi%6787%
6933:3+<"%%F'(2%3.1+B%;.%123%1'AC3%=+,K;/3<%123%,K3+'CC%FGGH%'E=C;1-/3D%A;./;.*%
(,.<1'.1%9;12%3++,+%'./%123%_
#"%%_3/%3.1+;3<%/;/%.,1%E'1(2%123%FGGH%<;*.%=+3/;(13/%AB%
123%E.3E,.;("%%^H%h%^,1%H313+E;.3/"%%RCC%E3'<-+3E3.1<%93+3%1')3.%'1%+,,E%
13E=3+'1-+3%;.%23I'.3<"%%623%A;./;.*%(,.<1'.1<%93+3%/313+E;.3/%-<;.*%\'C3;/'f+'=2%
'./%FN-'L,.%!!!"#%V]33%3I=3+;E3.1'CX"%%1,7A = +1339111 
± 14760.9832A = +43625866 ± 16000.99619A = -52428801 ± 14300.99776A = +556b32218 ± 18780.995294OHOH A = +294Ka = 4612 ± 182R2 = 0.99849A = +312220340 ± 11501
0.99709A = +944264760 ± 98090.997255OHOH6OHOH7OHOH9OHOH1,81,91,121,10A = +23918262 ± 4500.99981 A = +28612846 ± 4210.99911
 A = +23221064 ± 7610.9987A = +37724475 ± 25320.98937 A = + 1625220 ± 1890.99907A = +30229516 ± 24800.99367A = + 21734631 ± 7910.99927A = + 54418138 ± 10510.99686A =  + 2583068 ± 2310.99755A = +4915853 ± 5700.98999A = + 20640546 ± 8210.99953A = + 78024758 ± 6860.99918 A =  + 1338199 ± 7330.99709Trisignate
16698 ± 14130.99276A = + 14133257 ± 18430.99707A = + 232b38503 ± 29240.99559 A = +7514746 ± 1980.99841 A = +7342017 ± 1510.99615 A = +3169888 ± 1540.99962 A = +3533817 ± 2900.99312 A = +2006600300 ± 256090.99795A = +800691360 ± 143740.99959 A = +1683761990 ± 477900.9961A= +744224070 ± 47120.99945A= + 1844187670 ± 151270.99832 A = +2434288210 ± 239440.99253 A = +4091658170 ± 294350.99767 A = +3584586640 ± 105820.99957Tweezer
GlycolC3C4C5
C6
C7C8C9#d>;<=>&'((().+
%&;./;.*%(,.<1'.1<%0,+%(,E=C3I3<%,0%123%#D@%5%#D#?%'./%#D#>%*CB(,C<%9;12%123%Ga%
5%Gi%6787%6933:3+<"%%F'(2%3.1+B%;.%123%1'AC3%=+,K;/3<%123%,K3+'CC%FGGH%'E=C;1-/3D%
A;./;.*%(,.<1'.1%9;12%3++,+%'./%123%_
#"%%_3/%3.1+;3<%/;/%.,1%E'1(2%123%FGGH%<;*.%
=+3/;(13/%AB%123%E.3E,.;(%'./%AC-3%3.1+;3<%'+3%FGGH%E3'<-+3E3.1<%,0%C'+*3%

'E=C;1-/3"%RCC%E3'<-+3E3.1<%93+3%1')3.%'1%+,,E%13E=3+'1-+3%;.%23I'.3<"%%623%A;./;.*%
(,.<1'.1<%93+3%/313+E;.3/%-<;.*%\'C3;/'f+'=2%'./%FN-'L,.%!!!"#%V]33%3I=3+;E3.1'CX"
<2,93/%'%(,++3C'L,.%,0%\
-%9;12%123%
C3.*12%,0%
123%*CB(,C"%%8,+%123%(,E=C3I3<%,0%Gb5%'./%Gi54.5
678756933:3+<%9;12%123%<2,+13+%(2';.%*CB(,C<%V#D>5%12+,-*2%#Dc5X%123%A;./;.*%(,.<1'.1<%93+3%;.%
123%,+/3+%,0%#?
/%Z%92;(2%'*+33<%93CC%9;12%123%C;13+'1-+3%+3=,+13/%K'C-3"%%O,93K3+D%0,+%123%
C,.*3+%(2';.%*CB(,C<%V#D@5%12+,-*2%#D#>5X%123%\
-%K'C-3<%;.(+3'<3%#?%0,C/%1,%#?
&%Z"%%!.13+3<L.*CBD%
123%(,E=C3I3<%,0%Gb5%'./%Gi54.5678756933:3+<%9;12%123<3%/;,C<%=+,K;/3/%123%E,<1%;.13.<3%

FGGH%<;*.'C<"%%623%C'+*3+%A;./;.*%(,.<1'.1<%<-**3<1%12'1%'%L*213+D%E,+3%+;*;/%(,E=C3I%2'<%
0,+E3/%92;(2%9,-C/%C;E;1%123%.-EA3+%,0%(,.0,+E'L,.<%12'1%123%(,E=C3I%(,-C/%'((3<<"%%R%<E'CC%

.-EA3+%,+%=,<<;ACB%'%<;.*C3%(,.0,+E'L,.%,0%123%(,E=C3I%9,-C/%A3%0'K,+3/"%%62-<D%12;<%(,-C/%
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,0%123%=,+=2B+;.%],+31%A'./%;<%,A<3+K3/%V]33%G2'=13+%>D%8;*-+3%!!"iX"%%!0%123%=,+=2B+;.<%2'K3%
*+3'13+%/;<1'.(3%A31933.%123ED%'.%,K3+'CC%'%C'+*3%+3/%<2;j%;<%,A<3+K3/"%%8,+%'%<;.*C3%(C'<<%,0%
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C3'/%1,%123%=+,=,<'C%,0%123%A;./;.*%E,/3%;.%8;*-+3%!!!"i%R"%R%T`5`;<%<1-/B%,0%Ga54.5678756933:3+%9;12%13+E;.'C%/;'E;.3<%'./%(2;+'C%*CB(,C<%9'<%
(,./-(13/%;.%123%<'E3%0'<2;,."%%8,+%123%13+E;.'C%/;'E;.3<D%'%C;.3'+%/3=3./3.(3%A31933.%123%

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#dc<N-'+3<X"%%62;<%9,-C/%<-**3<1%12'1%<'E3%A;./;.*%E,/3%;<%,=3+'L,.'C%0,+%GU54.567756933:3+%
'./%Ga54.5678756933:3+%9;12%123%/;'E;.3%<-A<1+'13<"%%&-1D%0,+%123%#D
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+3C'L,.<2;=%A31933.%*CB(,C%C3.*12%'./%123%],+31%A'./%+3/%<2;j%9'<%,A<3+K3/%V8;*-+3%!!!"##%

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y = -31.701x + 23694!R" = 0.96984!y = -33.63x + 24032!R" = 0.97674!y = 3.2744x2 - 72.5x + 24289!R" = 0.99611
!23850!23900!23950!24000!24050!24100!24150!24200!23300!23400!23500!23600!23700!23800!23900!24000!2!4!6!8!10!!max (wavenumbers)!!max (wavenumbers)!Number of Methylene Units!Tweezer Soret Band Shift
!C5-Zn-TPP Diamine
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NBrPd source (x mol%)CuI (x mol%)diisopropylamine, N235 ¡C, 12 h+TMSH(1.1 equiv)NRxProductYield 
%Entry132III.20, 3-pyridyl, R = TMSIII.21, 2-pyridyl, R = TMSIII.22, 4-pyridyl, R = H542.55101010III.20III.20III.20III.21III.22003542NTMSIII.20, 3-pyridylIII.21, 2-pyridylMeOHK2CO3rt, 30 minNHIII.23, 3-pyridyl, 98%III.24, 2-pyridyl, 93%A:B:A, 3-pyridylB, 2-pyridylC, 4-pyridylStartingMaterialAAABCPd sourcePd(PPh3)2Cl2Pd(PPh3)4Pd(PPh3)4Pd(PPh3)4Pd(PPh3)2Cl217#U@789&:&'((()-+
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NNHIII.23, 3-pyridylIII.24, 2-pyridylIII.22, 4-pyridylCu(OAc)2.H2O (8.4 equiv)pyridine, O2, 40 ¡C, 24hNBrA, 3-pyridylB, 2-pyridylC, 4-pyridyl(1.1 equiv)Pd(PPh3)4 (10 mol%)CuI (10 mol%)diisopropylamine, N235 ¡C, 12 hNNNIII.25, 3,3'III.26, 2,2'III.27, 4,4'III.28, 3,3'III.29, 2,2'III.30, 4,4'ProductYield 
%Entry13254aa
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bIII.25III.26III.27III.28
III.2912593345StartingMaterial(s)III.23, AIII.24, BIII.22, CIII.23III.24Reactionab6III.22bIII.3021#Ui789&:&'((().+
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NNNNNNNNNNNNNNNNNNNNN2.8 †2.8 †5.6 †7.0 †5.2 †8.0 †9.4 †7.7 †10.5 †11.9 
†C3: 422.8 nmC5: 422.6 nmC3: 415.2 nmC5: 415.0 nmC3: No BindingC5: No BindingC3: 419.1 nmC5: 419.2 nmC3: 419.9 nmC5: 420.0 nmC3: No BindingC5: No BindingC3: No BindingC5: No BindingC3: 420.0 nmC5: 419.9 nmC3: 420.6 nmC5: 420.7 nmC3: 420.6 nmC5: 420.5 nmC3: 421.4 nmC5: 421.2 nm#c#!"#$%&'((()*0+'
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9/39-/6)&>-,&823&34-H@&(?)-2-?&7@78397&;682&LTE
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4,6/)64?3B&I,#&W6(-@-/+&X6&;(7&(<?3&8-&039-/78,(83&82(8&)26,(?&1UJ&)-/8(6/6/+&9-?3).?37&;6??&

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9-?3).?37&7@/82376:30&<@&I,#&Y./&Z(/&NJ6+.,3&!"#$P#!!&!/&823&7(93&536/B&68&;(7&2@4-82376:30&82(8&0383,96/(A-/&->&(<7-?.83&)-/G+.,(A-/&->&
)26,(?&9-?3).?37&)-/8(6/6/+&(&2383,-(,-9(A)&9-638@&72-.?0&(?7-&<3&4-776<?3&.76/+&823&
4-,42@,6/&8;33:3,7#&&L26,(?&4@,60@?&(?)-2-?7&(,3&->&+,3(8&6/83,378&6/&823&G3?07&->&(7@9938,6)&
OOOTBSOTBSOBnOH164421nm (+78)415nm (-59)A = +137OOOTBSOTBSOBnOH164422nm (+22)415nm (-11)
A = +33OOOTBSOTBSOBnOH164423nm (-14)415nm (+22)A = -36OOOTBSOHOBnOAc164424nm (-182)415nm (+92)A = -274$RO!"#$%&'()*+,
&KLLI&(/(?@767&->&()38-+3/6/&8@43&<67E1UJ&9-?3).?37&;682&LTED/E1FJFE
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",#"(&->&./()A5(830&(?*3/37&(7&72-;/&<@&Fe(8:&(/0&
NOHOH(1.5 equiv)+ Ti(OiPr)
4!OHPh3COOH(3 equiv)OHO64% ee1987: Sharpless and Co-workersNOHOArAr!Ar = !-naphthylNOHOArArLigandOHEt2Zn (3 equiv)Ligand (2 mol%)NaHOH93% ee1994: Hoshino and Co-workers$R$!"#$%&'()*-,&V7@9938,6)&7@/823767&;682&)26,(?&4@,60@?&(?)-2-?&?6+(/07#!"#!()-;-,*3,7#")#"*&&12373&(,3&73?3)830&3H(94?37&->&
4@,606/3&<(730&?6+(/07&>-,&-,+(/-938(??6)&
8,(/7>-,9(A-/7&2-;353,B&-823,&2383,-(,-9(A)&9-?3).?37&7.)2&(7&823&4@,606/3&<67E-H(:-?6/37&
NF@'fWP&?6+(/07&2(53&<33/&394?-@30&(7&938(?&?6+(/07&6/&(&5(,638@&->&(7@9938,6)&7@/823767&
6/)?.06/+&c6)2(3?&(006A-/7B
$+'$"&LEU&(96/(A-/7
$$&(/0&(??@?6)&7.<7A8.A-/
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-,+(/-)(8(?@767&4(,A).?(,?@&6/&-.,&?(<&>-,&823&0353?-493/8&->&823&(7@9938,6)&)2?-,-)@)?6:(A-/&
,3()A-/7#$&'$(&L26,(?&4@,60@?&(?)-2-?7&(,3&->&6/83,378&8-&823&42(,9()3.A)(?&6/0.78,@&(7&;3??&NJ6+.,3&!"#

gP#$)#$*&&f/3&->&823&G,78&,34-,87&,3+(,06/+&4@,60@?&(?)-2-?7&;(7&6/&$RhO&<@&F-*-,/@&(/0&)-E
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(7&(/A)-/5.?7(/8&()A568@&>-,&(&5(,638@&->&(,@?EgE4@,60@?&*38-/37#&&c-,3&,3)3/8?@B&(,@?E\E4@,60@?&
NPhHONPhO(Ph)2P1. Ph2PNEt22. [Ir(cod)Cl]2    NaBArFIrBArFIr complexIr complex (1 mol%)2h, 50 bar H294% ee2004: Pfaltz and Co-workersNOHONPh1997: Moberg and Co-workersLigandOOracemic[(allyl)PdCl]2 (2.5 mol%)Ligand (5 mol%)(MeOCO)2CH2, KOAcOOOO90% ee$R\!"#$%&'()*.,&KH(94?37&->&(7@9938,6)&7@/823767&;682&)26,(?&4@,60@?&(?)-2-?&?6+(/07#"&#"*(?)-2-?7&2(53&73,530&(7&6/83,9306(837&8-&
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HPhHOPy(S)HPyHOPh(R)!OHOMeOPh(R)-MPA
DCCDMAPHPhOPyOMeOPhHPyOPhOMeOPh(R,S)(R,R)PyHPhOMePhH(R,S)PhHPyOMePhH(R,R)No Change in Pyridine Chemical ShiftsUpfield Shift of the Pyridine a-protonDue to Shielding by the MPA 
Phenyl RingB: General Mnemonic:!
!HPyHOPhHPyOPhOMeOPhHPyOPhOMeOPh(R)-MPA
(S)-MPA
MPAO
H"#RS <0"#RS >0# of Pyridine $-protonfor the Two 
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Noyori Cat (5 mol%)HCO2H:Et3N (2:1)CH2Cl2, 24 h, r.t.
NHONC5H11OHNNNNC6F5C6F5C6F5OONNNNC6F5C6F5C6F5OOnn = 0, C3-Zn-TPFP-Tweezer
n = 2, C5-Zn-TPFP-Tweezer
n = 5, C8-Zn-TPFP-Tweezer
ZnZnNOH!1 mM Tweezer
Hexanes0 ¡CNC5H11O1. C5H11MgBr (5 equiv)    THF, 
3 h, Ar2. MnO2 (20 equiv)    THF, 
24 h, r.t.
A:B:n = 5, C8-Zn-TPFP-Tweezer 
A = -141n = 0, C3-Zn-TPFP-Tweezer, 
No ECCDn = 2, C5-Zn-TPFP-Tweezer, 
No ECCDIV.2a
(R)-IV.3a
(R)-IV.3a
-90!-40!10!60!380!400!420!440! 
!427 nm-80413 nm61$RR!"#$%&'()*2,'
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3,&[@/823767&->&
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4,&KLLI&;682&LQED/E1FJFE1;33:3,&(8&$&sc&8;33:3,&6/&23H(/37&(8&O&
.L&(/0&T&3M.65(?3/87&->&N"PE$EN\E4@,60@?P&23H(/E$E-?#-53,(??&(94?68.03&->&E$g$&;(7&-<73,530&;682&T
&3M.65(?3/87&->&823&)26,(?&(?)-2-?#&&123&/3)37768@&
>-,&823&LQ&?6/*3,&;6??&<3&067).7730&6/&7.<73M.3/8&73)A-/7#&S682&823&4,-->&->&)-/)348&)-94?3830B&3C-,87&8-&378(<?672&(&+3/3,(?&9/39-/6)&>-,&)26,(?&
2383,-(,-9(A)&(?)-2-?7&;(7&./03,8(*3/#&&V&73,637&->&)26,(?&7.<78,(837&;682&(&5(,638@&->&_E

7.<7A8.3/87&(/0&4@,60@?&7.<7A8.A-/&4(=3,/7&;3,3&,3M.6,30#&&123&7@/823767&->&823&)26,(?&
(?)-2-?7&;3,3&8-&>-??-;&823&82,33&7834&4,-)30.,3&037),6<30&(<-53&>-,&N
"PE$EN\E4@,60@?PE23H(/E$E-?#&&J6,78B&36823,&(/&(?*@?&-,&(,@?&u,6+/(,0&(00A-/&8-&823&(44,-4,6(83&4@,60@?&(?032@03&;-.?0&

4,-5603&823&,()396)&(?)-2-?7#&&12373&(?)-2-?7&;-.?0&823/&<3&-H606:30&8-&823&)-,,374-/06/+&
*38-/37&(/0&7.<73M.3/8&(7@9938,6)&,30.)A-/&->&823&*38-/3&;-.?0&+3/3,(83&823&)26,(?&4@,60@?&
9382(/-?7#&&12373&;-.?0&823/&<3&7.<^3)830&8-&KLLI&(/(?@767#
&\EB&dE&(/0&gE4@,60@?&)(,<-H(?032@037&;3,3&,3M.6,30&>-,&823&6/6A(?&u,6+/(,0&(006A-/7&8-&
())377&823&,()396)&(?)-2-?7#&&\E&(/0&gE4@,606/3&)(,<-H(?032@03&;3,3&(8&2(/0&(/0&dE4@,606/3&
)(,<-H(?032@03&;(7&M.6)*?@&())37730&>,-9&/6)-A/6)&()60&82,-.+2&(&82,33&7834&4,-8-)-?#&&

K783,6G)(A-/&->&/6)-A/6)&()60&;682&9382(/-?&./03,&()606)&)-/06A-/7B&XVU&,30.)A-/&->&823&
,37.?A/+&9382@?&3783,&(/0&823/&c/f
"&-H60(A-/&4,-56030&823&dE4@,60@?&)(,<-H(?032@03#&&123&
u,6+/(,0&(006A-/7&8-&823&4@,60@?&(?032@037&4,-)33030&;682&9-03,(83&8-&26+2&@63?07&6/&(??&)(737&

N1(<?3&!"#$P#&&J-,&823&23H(03)@?9(+/376.9&<,-9603B&06382@?&3823,&;(7&.730&6/783(0&->&1UJ&0.3&
8-&?-;&7-?.<6?68@&->&$E<,-9-23H(03)(/3&6/&1UJ#
&S682&823&,()396)&(?)-2-?7&6/&2(/0B&7353,(?&-H60(A-/&)-/06A-/7&;3,3&3H4?-,30&(7&
-H60(A-/&->&$EN\E4@,60@?PE23H(/E$E-?&N
()*+5
P&;682&c/f
"&6/&LU
"L?"&+(53&?-;&@63?07&->&823&*38-/3&
(k3,&gQ&2-.,7#&&
()*+5
&;(7&7.<^3)830&8-&)-99-/&)-/06A-/7&7.)2&(7&c/f
"&6/&1UJB&[;3,/B&F(,6*2E
I-3,6/+B&IcF&(/0&FLL#&&t/>-,8./(83?@B&[;3,/B&IcF&(/0&FLL&>(6?30&8-&4,-5603&823&0376,30&
\OO*38-/37&<.8B&c/f
"&(/0&F(,6*2EI-3,6/+&)-/
06A-/7&060&4,-5603&823&*38-/3B&;26)2&;(7&823/&
7.<^3)830&8-&823&i-@-,6&,30.)A-/#&&123&*38-/3&>,-9&823&c/f
"&-H60(A-/&;(7&7.))377>.??@&
,30.)30&./03,&823&i-@-,6&)-/06A-/7&2-;353,B&;23/&823&*38-/3&4,-0.)3&>,-9&823&F(,6*2E
I-3,6/+&-H60(A-/&;(7&7.<^3)830&8-&7.<73M.3/8&i-@-,6&,30.)A-/B&823&*38-/3&;(7&,3)-53,30#&&!8&
67&2@4-82376:30&82(8&823&069382@?&7.?G03&<6E4,-0.)8&->&823&F(,6*2EI-3,6/+&-H60(A-/&9(@&2(53&

<33/&4,373/8&;682&823&*38-/3#&&123&7.?G03&96+28&<6/0&8-&823&,.823/6.9&)(8(?@78&>-,&823&i-@-,6&
,30.)A-/&823,3<@&4,353/A/+&<6/06/+&(/0&,30.)A-/&->&823&*38-/3&(7&0376,30#&&123,3>-,3B&c/f
"&;(7&823&-H606:6/+&,3(+3/8&->&)2-6)3&4,-5606/+&())377&8-&823&4@,60@?&*38-/37&(7&,30.)A-/&->&823&
R-MgBrTHF, 
3 h, ArNHONROHProductYield 
%Entry1325a45467999837StartingAldehydeRTemp
6871091211178083954866522-pyridyl2-pyridyl2-pyridyl2-pyridyl2-pyridyl2-pyridyl2-pyridyl2-pyridyl3-pyridyl3-pyridyl4-pyridyl4-pyridylpentylpentylpentylphenylphenylphenylmethylisopropylsec-butylhexadecylmesityltolylr.t.
r.t.
r.t.
r.t.

r.t.
r.t.
reflux
reflux
refluxrefluxrefluxrefluxIV.1a
IV.1b
IV.1c
IV.1d
IV.1e
IV.1f
IV.1g
IV.1h
IV.1i
IV.1j
IV.1k
IV.1l
IV.1a-l
\O$6578&'()*+,'
u,6+/(,0&(006A-/7&8-&4@,60@?&(?032@037&8-&+653&823&,()396)&4@,60@?&(?)-2-?7&
N()*+59()*+8
P#&&(%&06382@?&3823,&;(7&823&7-?53/8&6/783(0&->&1UJ#*38-/3&>,-9&823&c/f
"&-H60(A-/&;(7&7.))377>.?#&&'@&)2(/+6/+&823&7-?53/8&8-&>,-9&LU
"L?"&8-&
1UJB&26+23,&@63?07&->&823&*38-/37&;(7&-<73,530#
&J-,&3()2&->&823&i-@-,6&,30.)A-/7B&(/&N
"P&)-/G+.,(A-/&->&823&4@,60@?&(?)-2-?&67&
4,306)830#&&i-@-,6&(/0&)-E;-,*3,7&2(53&72-;/&82,-.+2&3H43,693/8(?&(/0&)-94.8(A-/(?&

78.0637&82(8&823&(?)-2-?&+3/3,(830&>,-9&(&,30.)A-/&;682&(&,.823/6.9&)(8(?@78&<3(,6/+&(/&N
"B"PE06(96/3&N17IFKiP&;6??&4,-5603&823&(,-9(A)&(?)-2-?&->&N
"P&)-/G+.,(A-/#
,+&&[2-;/&6/&J6+.,3&!"#Q&
67&823&78,.)8.,3&->&823&)(8(?@78&.730&(/0&823&4,3>3,,30&8,(/76A-/&78(83#&&123&)-/>-,9(A-/&->&823&
G53E939<3,30&,6/+&)-/8(6/6/+&823&06(96/3&(/0&,.823/6.9&67&06)8(830&<@&823&783,3-)239678,@&
->&823&06(96/3#&&123&)-/>-,9(A-/&72-;/&67&4,3>3,,30&(7&823&423/@?&,6/+7&->&823&06(96/3&(,3&

3M.(8-,6(?#&&123&-H@+3/&->&823&*38-/3&2@0,-+3/&<-/07&;682&823&4,-8-/(830&(96/3&(/0&823&
4@,606/3&,6/+&67&82-.+28&8-&3/^-@&(&>(5-,(<?3&LUvl&6/83,()A-/&;682&823&93768@?3/3&->&823&
,.823/6.9&)-94?3H#&&123&2@0,603&67&823/&03?653,30&>,-9&823&,.823/6.9&8-&823&)(,<-/&->&823&

*38-/3&4,-5606/+&823&(?)-2-?&;26)2&6/&82373&)(737&;-.?0&<3(,&(/&N"P&)-/G+.,(A-/#
RuNHeqNTsHPhHPhHHaxOPyRNSOONH2RuClNoyori CatalystRuCl[(R,R)-TsDPEN]
(!6-mesitylene)PyORFavoredTSàPyOHHRPyHORHHCO2H:Et3N (2:1)\O\!"#$%&'()*:,
&[83,3-)239678,@&->&823&i-@-,6&,30.)A-/#&&[2-;/&(,3&823&)(8(?@78&.730B&823&
4,3>3,,30&8,(/76A-/&78(83&->&823&)(8(?@78&(/0&*38-/3&(/0&823&(?)-2-?&+3/3,(830&(k3,&
,30.)A-/#&&123&4,306)830&)-/G+.,(A-/&->&823&(?)-2-?&67&(7&72-;/#,+&123&(7@9938,6)&,30.)A-/&;(7&72-;/&8-&4,-5603&N
"PE$EN\E4@,60@?P&23H(/E$E-?&N
;8<9()*.5
P&6/&26+2&@63?0#&&123,3&;(7&7-93&)-/)3,/&2-;353,B&82(8&823&,30.)A-/&;-.?0&/-8&<3&3M.(??@&(7&
7.))377>.?&>-,&_E(,@?&4@,60@?&9382(/-/37#&&123&-.8)-93&->&823&i-@-,6&,30.)A-/&;682&j.N
$,E937A@?3/3PEN
"B"PE17IFKi&67&*/-;/&8-&<3&3C3)830&<@&823&603/A8@&->&823&_E7.<7A8.3/8&6/&83,97&
->&<-82&@63?0&(/0&3/(/A-73?3)A568@#&&!8&2(7&<33/&039-/78,(830&82(8&>-,&()38-423/-/3&823&
)-,,374-/06/+&(?)-2-?&67&+3/3,(830&;682&(&rRRa&@63?0&(/0&Rha&
%%&;23,3(7&,30.)A-/&->&
&E9382-H@423/@?E&E)@(/-423/@?*38-/3&./03,&603/A)(?&)-/06A-/7&4,-56037&(&Tga&@63?0&(/0&]]a&
%%&->&823&)-,,374-/06/+&(?)-2-?#
&*&&Z38B&823&,30.)A-/&;(7&(=394830&;682&423/@?E\E4@,60@?&
*38-/3#&&123&78(,A/+&*38-/3&;(7&,3)-53,30&(k3,&7353,(?&(=39487#&&123&L'[&,30.)A-/&->&

423/@?E\E4@,60@?&*38-/3&;(7&(?7-&(=394830&(/0&(+(6/&823&*38-/3&;(7&,3)-53,30#&&1(<?3&!"#\&
NROHMnO2(20 equiv)THF, 
24 h, r.t.
NRONoyori Cat(5 mol%)HCO2H:Et3N (2:1)CH2Cl2, 24 h, r.t.
NROHProductYield 
%Entry13254>9983766570StartingAlcoholProductYield 
%IV.3a
IV.3b
IV.3c
IV.3d
IV.3e
IV.1a-f
IV.2a-f
IV.3a-f
% eeIV.2a
IV.2b
IV.2c
IV.2d
IV.2e
IV.1a
IV.1b
IV.1c
IV.1d
IV.1e
70673730955400006aIV.3h
IV.2h
IV.1h
84050\Od6578&'()*-,
&j37.?87&->&c/f
"&-H60(A-/7&(/0&i-@-,6&(7@9938,6)&,30.)A-/7#&&F3,)3/8&
%%'&0383,96/30&<@&UFXL#7.99(,6:37&823&,37.?87&->&823&c/f
"&-H60(A-/7
&(/0&7.<73M.3/8&i-@-,6&,30.)A-/7&>-,&823&(?*@?E
4@,60@?&(?)-2-?7#&&t/>-,8./(83?@B&823&-/?@&7.))377>.?&i-@-,6&,30.)A-/&;(7&82(8&8-&+3/3,(83&823&
8378&7.<78,(83&N
;8<9()*.5
P#&&123,3>-,3B&-823,&9382-07&8-&-<8(6/&823&)26,(?&(?)-2-?7&;3,3&
3H4?-,30#&S682&823&>(6?.,3&->&823&(7@9938,6)&,30.)A-/&->&823&4@,60@?&*38-/37B&UFXL&734(,(A-/&
->&823&,()396)&(?)-2-?&;(7&(=394830#&&1267&4,-530&4,-<?39(A)&>-,&?(,+3&7)(?3&734(,(A-/7#&&123&
,383/A-/&A937&->&823&_E(?*@?&4@,60@?&(?)-2-?7&3/(/A-93,7&;3,3&8--&)?-73&8-&4,353/8&(&)?3(/&
734(,(A-/&;23/&)-/)3/8,(830&7(94?37&;3,3&6/^3)830&./03,&06C3,3/8&7-?53/8&96H8.,37B&e-;&

,(837&(/0&;682&06C3,3/8&)26,(?&)-?.9/7#&J6/(??@B&823&734(,(A-/&->&(&06(783,3-93,6)&96H8.,3&->&823&N
#PEcFV&3783,7&->&823&,()396)&
(?)-2-?&;(7&(=394830#&&1267&9382-0&;(7&(05(/8(+3-.7&6/&82(8B&823&06(783,3-93,7&->&823&

(?)-2-?7&)-.?0&<3&734(,(830&<@&4,34&1XL&(/0&823&(<7-?.83&)-/G+.,(A-/&->&823&(?)-2-?&;(7&
0383,96/30&.76/+&823&c-723,&3783,&83)2/6M.3&4,356-.7?@&037),6<30#
,,&&123&N
#PEcFV&3783,7&;3,3&
7@/82376:30&<@&KIL&9306(830&)-.4?6/+&->&823&,()396)&(?)-2-?&;682&N
#PE_E9382-H@E423/@?()3A)&

()60&(/0&823&,37.?A/+&06(783,3-93,6)&96H8.,3&;(7&734(,(830&<@&4,34&1XL#&&123&)-/G+.,(A-/&->&
823&4@,60@?&(?)-2-?&(/0&06(783,3-93,6)&,(A-&->&823&3783,&;(7&0383,96/30&>,-9&823&
!U&icj#&&
123&3783,7&;3,3&7.<^3)830&8-&2@0,-?@767&;682&$a&i(fU&6/&1UJ&(/0&823&a
%%&->&823&(?)-2-?&;(7&
0383,96/30&<@&UFXL&4,6-,&8-&KLLI&(/(?@767#&&1(<?3&!"#dvg&7.99(,6:37&823&@63?07B&
()*&(/0&a
%%&>-,&3()2&->&823&(?)-2-?7&-<8(6/30&.76/+&8267&4,-8-)-?#\OgNROHA. (S)-MPA 
(1.3 equiv)     DMAP 
(1.3 equiv)     EDC (1.3 equiv)     CH2Cl2, 12 h, r.t.
NROB.1. prep-TLC         separationB.2. 1% NaOH:THF        (1:1), 12 h, r.t.
NROHYield 
% (% ee)Entry24365StartingAlcoholYield 
%(R)-IV.3b
(S)-IV.3b
(R)-IV.3c
(S)-IV.3c
(R)-IV.3d
(S)-IV.3d
(R)-IV.3e
(S)-IV.3e
(R)-IV.3f
(S)-IV.3f
IV.1a-g
(R,S)-IV.4a-g
(R)-3a-gIV.1b
IV.1c
IV.1d
IV.1e
IV.1f
OOMeNROOOMe(S,S)-IV.4a-g
!NROH(S)-3a-gorIV.4b
IV.4c
IV.4d
IV.4e
IV.4f
746756774775 (2:1)56 (1:2)31 (4:1)33 (0:1)57 (1:0)64 (0:1)80 (2:1)98 (0:1)71 (20:1)>99 (0:1)33 (ND)a33 (ND)NA>99 (>99)71 (>99)60 (>99)51 (67)64 (>99)>99 (95)89 (>99)1(R)-IV.3a
(S)-IV.3a
IV.1a
IV.4a
9962 (4:1)98 (0:1)86 (80)99 (>99)7(R)-IV.3g
(S)-IV.3g
IV.1g
IV.4g
8945 (4:1)50 (0:1)NA>99 (>99)(R,S)-IV.4b
(S,S)-IV.4b
(R,S)-IV.4c
(S,S)-IV.4c
(R,S)-IV.4d
(S,S)-IV.4d
(R,S)-IV.4e
(S,S)-IV.4e
(R,S)-IV.4f
(S,S)-IV.4f
(R,S)-IV.4a
(S,S)-IV.4a
(R,S)-IV.4g
(S,S)-IV.4g
Yield 
%(dr (R,S):(S,S))ProductAProductB.1ProductB.2\OT6578&'()*.,'
[@/823767&->&N
#PEcFV&K783,7&(/0&7.<73M.3/8&2@0,-?@767&@63?06/+&)26,(?&_E(?*@?&
4@,60@?&(?)-2-?7#&&V<7-?.83&783,3-)239678,@&(/0&06(783,3-93,6)&,(A-7&;3,3&0383,96/30&
<@&
!U&icj#&&K/(/A-93,6)&3H)377&;(7&0383,96/30&<@&)26,(?&UFXL&NVIEUB&R]%g&
23H(/37%+F,fUB&O#T&9Xv96/P#&&(%&K/(/A-93,7&)-.?0&/-8&<3&,37-?530&;682&UFXL#&&iI%&i-8&
0383,96/30#&&iV%&i-8&V44?6)(<?3#
&!/&(006A-/&8-&823&7@7839(A)&78.0@&->&4@,60@?&(?)-2-?7B&(/&3H(94?3&6??.78,(A/+&823&
(44?6)(A-/&->&823&KLLI&(/(?@767&;682&(&9-,3&)-94?3H&9-?3).?3&;(7&0376,30#&&V/&67-M.6/-?6/3&
)-/8(6/6/+&/(8.,(?&4,-0.)8&67-?(830&6/&\O$O&<@&V;(/+&(/0&)-E;-,*3,7&>,-9&
,%+-*./0+%(+1'
2)%3+&%*
&;(7&)2-73/&(7&(/&603(?&)(/060(83&8-&72-;&823&3H83/76-/&->&823&KLLI&9382-0-?-+@&
2143(R)-IV.3h
(S)-IV.3h
(R)-IV.3i
(S)-IV.3i
(R)-IV.3j
(S)-IV.3j
(R)-IV.3k
(S)-IV.3k
IV.1h
IV.1i
IV.1j
IV.1k
IV.4h
IV.4i
IV.4j
IV.4k
9696956065 (10:1)79 (0:1)>99 (3:1)91 (0:1)>99 (10:1)>99 (1:20)>99 (10:1)>99 (1:20)96 (91)99 (>99)76 (75)>99 (>99)>99 (91)>99 (95)37 (91)29 (95)5(R)-IV.3l
(S)-IV.3l
IV.1l
IV.4l
9941 (4:1)50 (0:1)>99 (80)>99 (>99)(R,S)-IV.4h
(S,S)-IV.4h
(R,S)-IV.4i
(S,S)-IV.4i
(R,S)-IV.4j
(S,S)-IV.4j
(R,S)-IV.4k
(S,S)-IV.4k
(R,S)-IV.4l
(S,S)-IV.4l
Yield 
% (% ee)EntryStartingAlcoholYield 
%!Yield 
%(dr (R,S):(S,S))ProductAProductB.1ProductB.2NROHA. (S)-MPA 
(1.3 equiv)     DMAP 
(1.3 equiv)     EDC (1.3 equiv)     CH2Cl2, 12 h, r.t.
NROB.1. prep-TLC         separationB.2. 1% NaOH:THF        (1:1), 12 h, r.t.
NROHIV.1h-l
(R,S)-IV.4h-l
(R)-3h-lOOMeNROOOMe(S,S)-IV.4h-l
!NROH(S)-3h-lor\O]6578&'()*/,'
[@/823767&->&N
#PEcFV&K783,7&(/0&7.<73M.3/8&2@0,-?@767&@63?06/+&)26,(?&_E(,@?&
4@,60@?&(?)-2-?7#&&V<7-?.83&783,3-)239678,@&(/0&06(783,3-93,6)&,(A-7&;3,3&0383,96/30&
<@&
!U&icj#&&K/(/A-93,6)&3H)377&;(7&0383,96/30&<@&)26,(?&UFXL&NVIEUB&R]%g&
23H(/37%+F,fUB&O#T&9Xv96/P#
>,-9&79(??&)26,(?&<.6?06/+&<?-)*7&8-&9-?3).?37
&;682&+,3(83,&)-94?3H68@#
(+&&123&78,.)8.,3&
4B4E069382@?(//-)23,6/&VB&(7&0383,96/30&<@&icj&(/(?@767B&67&(&8,67E9382-H@&7.<7A8.830&_E(,@?&
67-M.6/-?6/3&(?)-2-?&NJ6+.,3&!"#RP#&&123&(.82-,7&0383,96/30&823&)-/G+.,(A-/&->&823&/(8.,(??@&
-)).,6/+&3/(/A-93,&8-&<3&
#&82,-.+2&823&KLLI&4,-8-)-?&,34-,830&<@&[/(8:*3&(/0&)-E;-,*3,7#
,%#,*&&V8&823&)-,3&->&
4B4E069382@?(//-)23,6/&V&67&N
#PE_E423/@?E\E4@,60@?9382(/-?&823,3>-,3B&68&
;(7&2@4-82376:30&82(8&823&76+/&->&823&KLLI&76+/(?&>-,&823&/(8.,(?&4,-0.)8&(/0&N
#PENnPE_E423/@?E\E4@,60@?9382(/-?&72-.?0&<3&823&7(93#&123&7@/823767&->&
4B4E069382@?(//-)23,6/&V&<3+(/&;682&(&FLL&-H60(A-/&->&823&
)-993,)6(??@&(5(6?(<?3&53,(8,@?&(?)-2-?&NdBgE069382-H@<3/:@?&(?)-2-?P&8-&53,(8,@?&(?032@03&
N[)2393&!"#$P#&&123&(?032@03&;(7&823/&7.<^3)830&8-&(/&(?0-?&)-/03/7(A-/&;682&/68,-9382(/3&
4,-5606/+&823&/68,-&78,@3/3B&N
5PE$B\E069382-H@EgEN\E/68,-56/@?P<3/:3/3&6/&hQa&@63?0&>-,&823&8;-&

78347#(!&&1267&;(7&,30.)30&8-&823&7(8.,(830&(96/3&;682&XVU&(/0&4,-83)830&;682&()38@?)2?-,603&
4,-5606/+&823&
6E()38@?E$B\E069382-H@EgEN\E(96/-382@?P<3/:3/3&6/&Qga&@63?0&>-,&823&8;-&78347#&&
Vk3,&7-93&-4A96:(A-/B&(&FfL?
$&)(8(?@:30&'67)2?3,Ei(463,(?7*6&032@0,(A53&)@)?6:(A-/&+(53&(&
RTa&@63?0&->&823&062@0,-67-M.6/-?6/3#
("&&!/6A(??@B&823&062@0,-67-M.6/-?6/3&;(7&8-&<3&-H606:30&8-&
NOHOOONOH(S)-(+)-IV.1h
(S)-(+)-!-phenyl-2-pyridylmethanol(S)-(+)-IV.5
(S)-(+)-O,O-dimethylannocherin A\Oh!"#$%&'()*=,'
123&78,.)8.,3&->&
4B4E069382@?(//-)23,6/&V#
(+&&123&72(,30&)-,3&->&823&
/(8.,(?&4,-0.)8&;682&N
#PE_E423/@?E\E4@,60@?9382(/-?&67&26+2?6+2830&6/&<?.3#&&12373&
9-?3).?37&(,3&3H43)830&8-&2(53&7696?(,&KLLI&,37.?87#823&
67-M.6/-?6/3&./03,&032@0,-+3/(A-/&)-/06A-/7&(/0&(&73)-/0&-H60(A-/&;682&[3f
"&8-&;(7&8-&
@63?0&823&0376,30&67-M.6/-?6/3&(?032@03&>-,&823&>-??-;6/+&u,6+/(,0&(006A-/#&&fH60(A-/&->&823&
062@0,-67-M.6/-?6/3&;(7&(=394830&./03,&(&5(,638@&->&)-/06A-/7&N1(<?3&!"#TP#
($'(,&&I62@0,-M.6/-?6/3&6/&823&4,373/)3&->&(6,&-,&-H@+3/&6/&Ic[f&-,&IcV&4,-56030&?-;&@63?07&->&823&

67-M.6/-?6/3&;682&7353,(?&./603/AG(<?3&03)-94-76A-/&4,-0.)87#&&J-,8./(83?@B&-H60(A-/&->&823&
062@0,-67-M.6/-?6/3&;682&c/f
"&6/&,3e.H6/+&)2?-,-<3/:3/3&4,-56030&(&734(,(<?3&96H8.,3&->&823&
67-M.6/-?6/3&(/0&823&67-M.6/-?6/3&(?032@03#
(&#(,&&J.,823,&-4A96:(A-/&->&823&c/f
"&-H60(A-/&
;(7&)-/0.)830&<@&5(,@6/+&823&(9-./8&->&823&-H60(/8&4,373/8&(/0&)2(/+6/+&823&7-?53/8#&&!8&;(7&
>-./0&82(8&\O&3M.65(?3/87&->&c/f
"&(/0&)2?-,-<3/:3/3&;3,3&<378&>-,&+3/3,(A-/&->&823&0376,30&
(?032@03&;682-.8&76+/6G)(/8&03)-94-76A-/#&&1267&,-.83&;(7&)2-73/&353/&82-.+2&(8&9-78&dOa&
OOHOOONO2OOHNOOONHHOOONOHO1. PCC (1.1 equiv)    CH2Cl2, r.t., 
8 h2. MeNO2 (5 equiv)    NH4OAc (1 equiv)    AcOH, reflux,     1.5 h    78% (2 steps)1. LAH (2 equiv)    THF,
 reflux, N2     3 h2. AcCl (1.2 equiv)    Et3N (1 equiv)    CH2Cl2, r.t., 
N2    8 h    84% (2 steps)OONIV.6
IV.7
IV.8
POCl3(1.5 equiv)toluenerefluxN2, 1 h95%IV.9
(±)-IV.5
(±)-O,O-dimethyl-annocherin AMnO2 (20 equiv)PhCl, reflux 18 h57%OMgBr(5 equiv)THF, 
reflux, Ar, 
4 h70%\OQ>?@&A&'()*+,
&[@/823767&->&,()396)&4B4E069382@?(//-)23,6/&V#->&823&(?032@03&;(7&67-?(830#&&
123&4.,6G30&67-M.6/-?6/3&;(7&7.<^3)830&8-&[3f
\&-H60(A-/&
)-/06A-/7&2-;353,B&-/?@&03)-94-76A-/&;(7&-<73,530#
((&&S682&823&(?032@03&6/&2(/0B&(006A-/&
->&
&E9382-H@423/@?9(+/376.9&<,-9603&4,-56030&823&,()396)&
4B4E069382@?(//-)23,6/&V#&&123&
3/(/A-93,7&;3,3&734(,(830&<@&)26,(?&UFXL#&S682&823&)-94?3A-/&->&823&7@/823767&->&
4B4E069382@?(//-)23,6/&VB&7@/823767&->&823&_E
)26,(?&4@,60@?&(?)-2-?7&;(7&)-/)?.030#&&'36/+&82(8&823&KLLI&(/(?@767&->&823&$B
!E+?@)-?7&
039-/78,(830&82(8&KLLI&)-.?0&<3&-<73,530&>-,&7.<78,(837&6/&;26)2&823&<6/06/+&76837&(,3&

734(,(830&<@&(&/.9<3,&->&)(,<-/&./687B&4@,60@?&(?)-2-?7&;682&823&2@0,-H@?&+,-.4&9-530&8-&823&

`E&-,&wE)(,<-/&;3,3&(?7-&7@/82376:30&N[)2393&!"#\P#&&123&(/6-/&->&\E46)-?6/3&67&3(76?@&+3/3,(830&
OONIV.8
OONHOIV.9
Conv. 
%Entry13254100100100100OxidantSolvent6100DMSODMSOairairMnO2 (10 equiv)OONIV.10
!oxidantsolventreflux, 12 hO2O2DMADMAMnO2 (20 equiv)MnO2 (30 equiv)MnO2 (85 equiv)MnO2 (20 equiv)879PhClPhClPhClPhCltoluene100100100IV.9:IV.10
500:10:10:11:22:11:10:1Total 
Yield
IV.9 
+ IV.10
 (%)246618757372>51250NDND\OR6578&'()*0,
&f4A96:(A-/&->&062@0,-67-M.6/-?6/3&-H60(A-/#NOHNOHNNHHnBuLi (2 equiv)Et2O, 0 ¡C!r.t.
N2, 1 hO(2.5 equiv)Et2O, 0 ¡C!r.t.
N2, 4 h, 63%(2.5 equiv)MgBr2 (2.75 equiv)Et2O, 0 ¡C!r.t.
N2, 4 h, 81%HOIV.11
(R)-IV.13
NOOMeONOOMeONOHNOHNNHHnBuLi (2 equiv)Et2O, 0 ¡C!r.t.
N2, 1 h1. (S)-MPA 
(1.3 equiv)     DMAP 
(1.3 equiv)     EDC (1.3 equiv)     CH2Cl2, 12 h, r.t.
2. Prep-TLC separation!1% NaOH:THF (1:1) 12 h, r.t.
(R,S)-IV.12
62%, 10:1 dr(S,S)-IV.12
62%, 20:1 drA:B:1% NaOH:THF (1:1) 12 h, r.t.
(R)-IV.11
>99%, 91% ee(S)-IV.11
90%, 95% ee\$O>?@&A&'()*-,'
[@/823767&->&
`E&(/0&wE&
4@,60@?&(?)-2-?7#&
3,&V006A-/&->&23H(/(?&8-&\E46)-?(83&
(/6-/&(/0&7.<73M.3/8&cFV&3783,&+3/3,(A-/&734(,(A-/&(/0&2@0,-?@767#&
4,&V006A-/&
4,-4@?3/3&-H603&8-&\E46)-?(83&(/6-/#<@&034,-8-/(A-/&->&823&_E9382@?&;682&
!E<.8@??6826.9#
()#(*&&V006A-/&->&23H(/(?&8-&823&\E
46)-?(83&(/6-/&4,-56030&823&,()396)&`E2@0,-H@4@,606/3B&$EN\E4@,60@?PE2348(/E\E-?&N
()*++
P&6/&Q$a&
@63?0#&&123&(006A-/&->&N
"PE4,-4@?3/3&-H603&8-&823&\E46)-?(83&(/6-/&+(53&823&wE2@0,-H@4@,606/3B&
N\"PEgEN\E4@,60@?PE<.8(/E\E-?&N
()*+-
P&6/&]da&@63?0#&&123&783,3-)239678,@&->&
()*++
&;(7&0383,96/30&
.76/+&823&c-723,&3783,&4,-8-)-?&037),6<30&>-,&823&_E)26,(?&4@,60@?&(?)-2-?7#&S682&82373&4@,606/3&<(730&)26,(?&(?)-2-?7&(8&2(/0B&3H4(/76-/&->&823&7.<78,(83&7)-43&8-&
-823,&2383,-(,-9(A)&(?)-2-?7&;(7&0376,30#&&!/6A(?&(=39487&8-&7@/82376:3&823&4@,,-?3&(/0&>.,(/&

<(730&(?)-2-?7&4,-530&4,-<?39(A)#&&S682&4@,,-?3&(/0&>.,(/&,3(06?@&(5(6?(<?3B&(&8;-E7834&
J,6303?EL,(k7&()@?(A-/&8-&6/78(??&(/&()38@?&+,-.4&>-??-;30&<@&(7@9938,6)&,30.)A-/&.76/+&(&L'[&
-,&i-@-,6&(7@9938,6)&,30.)A-/&;(7&3/5676-/30#&&J,6303?EL,(k7&()@?(A-/&->&4@,,-?3&;682&

()38@?)2?-,603&(/0&:6/)&0.78&4,-56030&(&96H8.,3&->&\E&(/0&dE()38@?4@,,-?3&N[)2393&!"#dP#&&12373&
;3,3&734(,(<?3&<@&)-?.9/&)2,-9(8-+,(42@&8-&+653&\Ta&@63?0&->&823&\E()38@?4@,,-?3&N
()*+/
P#)+#)!&&123&L'[&,30.)A-/&->&
()*+/
&;(7&(=394830&<.8&823&0376,30&(?)-2-?&;(7&/-8&+3/3,(830#&&!8&
;(7&2@4-82376:30&82(8&823&>,33&/68,-+3/&->&823&4@,,-?3&)-.?0&<3&)--,06/(A/+&;682&823&<-,-/&->&

823&)(8(?@78&823,3<@&4,353/A/+&823&,30.)A-/&->&823&*38-/3#&&12.7B&823&4@,,-?3&;(7&7.<^3)830&8-&
'-)&4,-83)A-/#
)!&&123&L'[&,30.)A-/&->&823&
6E'-)E\E()38@?4@,,-?3&N
()*+0
P&;(7&(=394830&(+(6/&
2-;353,B&823&*38-/3&;(7&,3)-53,30#&&
6Ec382@?4@,,-?3&;(7&(?7-&(5(6?(<?3&(/0&()38@?(A-/&;682&
()38@?)2?-,603&(/0&:6/)&!!&8,6e(83&+(53&
6E9382@?E\E()38@?4@,,-?3&N
()*+1
P&6/&\Oa&@63?0#
)"&&1267&
*38-/3&;(7&7.<^3)830&8-&i-@-,6&,30.)A-/&)-/06A-/7#&&t/>-,8./(83?@B&(+(6/&823,3&;(7&/-&
35603/)3&->&823&0376,30&(?)-2-?&<@&icj#&&
\$$&!/&-823,&(=39487&8-&+3/3,(83&(&4@,,-?@?(?)-2-?B&4@,,-?3E\E)(,<-H(?032@03&;(7&
4,-83)830&;682&8-7@?&)2?-,603B&+3/3,(A/+&
6E8-7@?E4@,,-?3E\E)(,<-H(?032@03&N
()*+2
P&823/&
(006A-/&->&423/@?9(+/376.9&<,-9603&4,-56030&,()396)&_EN
6E8-7@?E\E4@,,-?@?PE<3/:@?(?)-2-?&N()*+:
P&6/&]]a&@63?0&>-,&823&8;-&78347&N[)2393&!"#gP#&&[696?(,?@B&(006A-/&->&9382@?9(+/376.9&

<,-9603&8-&823&4@,,-?@?(?032@03&+(53&_EN
6E8-7@?E\E4@,,-?@?PE382(/-?&N
()*+=
P&6/&d]a&@63?0&-53,(??#&&
12373&8;-&,()396)&(?)-2-?7&;3,3&7.<^3)830&8-&cFV&3783,6G)(A-/&823/&734(,(A-/&<@&4,34E1XL#&&

t/>-,8./(83?@B&/36823,&823&3783,&-,&823&(?)-2-?&N6/&823&353/8&82(8&2@0,-?@767&-)).,,30&-/&823&

1XLP&;3,3&0383)830#&&V8&8267&4-6/8&823&7@/823767&->&_E)26,(?&4@,,-@?&(?)-2-?7&;(7&(<(/0-/30#HNHNOZn dust (2 equiv)toluene, r.t., 
N2, 1 h25%OCl(1.5 equiv)BocNO(S)-CBS Reagent (10 mol%)BH3!SMe2 (0.7 equiv)r.t., 
N2, 1 hHNOH(Boc)2O (1.1 equiv)NaH (1.2 equiv)THF, 
r.t., 
N2, 14 h90%(S)-CBS Reagent (10 mol%)BH3!SMe2 (0.7 equiv)r.t., 
N2, 1 hBocNOH(R)-CBS Reagent (10 mol%)BH3!SMe2 (0.7 equiv)r.t., 
N2, 1 hBocNOHNBOHPhPhCH3(S)-CBS ReagentNNOZn(OTf)2 (0.1 equiv)MeNO2, r.t., 
N2, 4 h17%OCl(1.5 equiv)Noyori cat (5 mol%)HCO2H:Et3N (2:1)r.t., 
N2, 24 hNOH!"#$%
IV.15
IV.16
\$\>?@&A&'()*.,
&J(6?30&(=39487&8-&7@/82376:3&->&
_E2@0,-H@&4@,,-?37&.76/+&(7@9938,6)&
,30.)A-/7#
&[696?(,&9382-0-?-+637&;3,3&823/&394?-@30&>-,&823&7@/823767&->&823&>.,(/&<(730&)26,(?&
(?)-2-?7&N[)2393&!"#TP#&&J,6303?EL,(k7&()@?(A-/&;(7&(=394830&;682&>.,(/&8-&+3/3,(83&\E
()38@?>.,(/#&&123&.73&->&()38@?)2?-,603&6/&823&4,373/)3&->&:6/)&!!&8,6e(83&+3/3,(830&\E()38@?>.,(/&
N()*+-B
P&6/&$Qa&@63?0#
)"&&123&7.<73M.3/8&i-@-,6&,30.)A-/&;(7&7.))377>.?&4,-5606/+&823&(?)-2-?B&
;8<9()*-+
B&6/&hQa&@63?0&(/0&R]a&
%%#)$&&V&73)-/0&>.,@?&(?)-2-?&;(7&7@/82376:30&>,-9&>.,(/E\E
)(,<-H(?032@03&>-??-;6/+&823&u,6+/(,0&(006A-/B&c/f
"&-H60(A-/
)%B&i-@-,6&,30.)A-/&037),6<30&
>-,&823&4@,60@?&(?)-2-?7#&&123&)26,(?&(?)-2-?B&$
"EN\E>.,@?PE23H(/E$E-?&N
;8<9()*-.
PB&;(7&67-?(830&6/&
\a&@63?0&-53,(??&(/0&rRTa&
%%&<(730&-/&-4A)(?&,-8(A-/#
)&&&J6/(??@B&$
"EN\E826423/@?PE382(/E$E-?&HNNOHHOTsCl 
(1.1 equiv)NaH (1.2 equiv)THF, 
r.t., 
Ar, 
12 h80%TsIV.18
NHOPhMgBr (5 equiv)THF, 
reflux, Ar, 
3 h82%MeMgBr(5 equiv)THF, 
r.t. 
Ar, 
3 h45%NOHTsIV.19
IV.17
TsNOHTs(S)-IV.18
NOHTs(R)-IV.18
1. (S)-MPA 
(1.3 equiv)     DMAP 
(1.3 equiv)     EDC (1.3 equiv)     CH2Cl2, 12 h, r.t.
2. prep-TLC     separation3. 1% NaOH:THF (1:1)     12 h, r.t.
NOHTs(S)-IV.19
NOHTs(R)-IV.19
1. (S)-MPA 
(1.3 equiv)     DMAP 
(1.3 equiv)     EDC (1.3 equiv)     CH2Cl2, 12 h, r.t.
2. prep-TLC     separation3. 1% NaOH:THF (1:1)     12 h, r.t.
\$d>?@&A&'()*/,
&[@/823767&->&823&
_E2@0,-H@&4@,,-?37&>-??-;6/+&823&4,-8-)-?&>-,&
_E2@0,-H@&
4@,606/37#&&L26,(?&(?)-2-?7&;3,3&8-&<3&())37730&82,-.+2&cFV&3783,6G)(A-/B&734(,(A-/&->&
06(783,3-93,7&823/&<(76)&2@0,-?@767&->&823&3783,#&&t?A9(83?@&8267&;(7&./7.))377>.?#N;8<9()*-/
P&;(7&67-?(830&6/&rRRa&@63?0
&(/0&R]a&
%%&N<(730&-/&-4A)(?&,-8(A-/P&>,-9&823&i-@-,6&
,30.)A-/&->&823&)-993,6)(??@&(5(6?(<?3&\E()38@?826-423/3#),&&&6E9382@?4@,,-?3&(/0&>.,(/&;3,3&(?7-&>./)A-/(?6:30&;682&(&`E2@0,-H@&(?*@?&7.<7A8.3/8&
<@&06,3)830&034,-8-/(A-/&;682&
!'.X6&6/&823&4,373/)3&->&1cKIV&N[)2393&!"#]P#
)(&&f4A)(??@&
4.,3&4,-4@?3/3&-H603&;(7&823/&(0030&8-&823&(/6-/&+3/3,(A/+&N\
#PE$EN\E6E9382@?4@,,-?@?PE4,-4(/E\E-?&N
;2<9()*-0
PB&
N\"PE$EN\E6E9382@?4@,,-?@?PE4,-4(/E\E-?&N
;8<9()*-0
PB&(/0&N\
#PE$EN\E>.,@?PE
OOHOOOOHOOC5H11OHZn dust (2 equiv)toluene, r.t., 
N2, 1 hOCl(1.5 equiv)Zn(OTf)2 (0.1 equiv)MeNO2, r.t., 
N2, 4 h18%OCl(1.5 equiv)Noyori cat (5 mol%)HCO2H:Et3N (2:1)r.t., 
N2, 24 h78%, 96% eeNoyori cat (5 mol%)HCO2H:Et3N (2:1)r.t., 
N2, 24 h10%, >95% eeOC5H11O1. C5H11MgBr (5 equiv)    THF, 
reflux, Ar, 
3 h     61%2. MnO2 (20 equiv)    CH2Cl2, r.t.
    34% brsmIV.20
(R)-IV.21
IV.22
(R)-IV.23
SOHSONoyori cat (5 mol%)HCO2H:Et3N (2:1)r.t., 
N2, 24 h>99%, 96% ee(R)-IV.24
\$g>?@&A&'()*0,'
[@/823767&->&)26,(?&>.,@?&(?)-2-?7#&&12373&;3,3&())37730&<@&i-@-,6&
,30.)A-/&->&823&)-,,374-/06/+&*38-/37#4,-4(/E\E-?&N
;2<9()*-1
P))&6/&9-03,(83&@63?07#
&&1267&)-94?3830&823&7@/823767&->&823&)26,(?&
2383,-(,-9(A)&(?)-2-?7&>-,&8267&78.0@#!"#g%&KLLI&[8.0@&->&823&L26,(?&U383,-(,-9(A)&V?)-2-?7'S682&823&7.<78,(837&6/&2(/0B&823&t"E"67&(/0&KLLI&78.0637&;3,3&)-/0.)830#&&!/6A(??@B&(&
t"E"67&A8,(A-/&;682&\E46)-?6/3&;(7&)-/0.)830&8-&-<8(6/&823&[-,38&<(/0&726k&N$$&/9P&(/0&823&

<6/06/+&)-/78(/8&>-,&(/&74
"&/68,-+3/&N$#T&H&$O
&&c'!P&;682&823&LQED/E1FJFE1;33:3,&N733&
3H43,693/8(?&>-,&+,(427&>,-9&t"E"67&A8,(A-/&(/0&<6/06/+&)-/78(/8&)(?).?(A-/
)*P#&&123&[-,38&
726k&N]&/9P&(/0&<6/06/+&)-/78(/8&N$O
&&c'!P&>-,&(&9-/-(?)-2-?&;(7&4,356-.7?@&0383,96/30#
)&&123&)-9<6/(A-/&->&8267&0(8(&6/06)(837&82(8&>-,&(/@&4@,60@?&(?)-2-?&)-94?3H37B&(&9(H69.9&[-,38&
<(/0&726k&->&$$&/9&)(/&<3&3H43)830#&&V?7-B&823&<6/06/+&)-/78(/8&0(8(&72-;7&82(8&823&4@,606/3&
MeNOHMeNnBuLi (1 equiv)TMEDA 
(1 equiv)Et2O, 0 ¡C!r.t.
N2, 1 hMeNOEt2O, 0 ¡C!r.t.
N2, 4 h, 35%OEt2O, 0 ¡C!r.t.
N2, 4 h, 47%MeNOHOnBuLi (1.7 equiv)TMEDA 
(1 equiv)Et2O, 0 ¡C!r.t.
N2, 1 hO(S)-IV.25
(R)-IV.25
OEt2O, 0 ¡C!r.t.
N2, 4 h, 32%OOH(S)-IV.26
(0.9 equiv)(0.9 equiv)(2.6 equiv)\$T>?@&A&'()*1,'
[@/823767&->&$EN\E
6E9382@?4@,,-?@?PE4,-4(/E\E-?&(/0&$EN\E>.,@?PE4,-4(/E\E
-?&.76/+&(&1cKIV&06,3)830&034,-8-/(A-/#NOH13NOHNOHNn-C5H11OH(R)-IV.3a
80% ee(R)-IV.3b
66% ee(S)-IV.3d
> 95% ee(R)-IV.3e
> 95% eeEntryPyridylAlcohol1325a4Expected SignObserved ECCD! nm ("#)Nn-C5H11OH(S)-IV.3a
> 95% eeNOH(S)-IV.3b
66% eeNOH(S)-IV.3c
> 95% ee6a7a8bEntryPyridylAlcoholExpected SignObserved ECCD! nm ("#)428 (+74)414 (-49)A = +123428 (-30)414 (+31)A = -61No ECCDNo ECCD425 (-32)418 (+28)A = -60428 (+35)415 (-22)A = +57426 (+51)415 (-34)A = +85429 (-26)414 (+22)A = -48NOH(R)-IV.3d
> 95% ee\$]6578&'()*1,'
KLLI&0(8(&>-,&(?*@?&7.<7A8.830&)26,(?&4@,60@?&(?)-2-?7#&&123&3H43)830&76+/7&
(,3&(&,37.?8&->&823&9/39-/6)7&0353?-430#&&V??&93(7.,393/87%&23H(/37B&O&
.LB&\&sc&
8;33:3,B&$O&3M.65(?3/87&->&7.<78,(83#&(%&]O&3M.65(?3/87&->&7.<78,(83#&<%&\&3M.65(?3/87&->&
7.<78,(83#/68,-+3/&<6/07&;682&823&:6/)&)3/83,&->&823
&4-,42@,6/7&(44,-H69(83?@&
(7&78,-/+&(7&823&2@0,-H@?&
-H@+3/#
Nn-C5H11OH(R)-IV.3f
95% eeNn-C5H11OH(R)-IV.3g
80% eeNOHNOH(R)-IV.11
90% ee(R)-IV.12
> 95% eeNOH13(S)-IV.3e
66% ee9429 (+90)415 (-61)A = +151n-C5H1110b121114131516Nn-C5H11OH(S)-IV.3f
> 95% eeNn-C5H11OH(S)-IV.3g
> 95% eeNOH(S)-IV.11
95% een-C5H11427 (-48)415 (+64)A = -112
425 (+26)417 (-33)A = +59426 (+234)415 (-127)A = +361426 (-198)415 (+111)
A = -309427 (-43)415 (+43)A = -86429 (+85)414 (-38)A = +88422 (+28)411 
(-17)A = +45EntryPyridylAlcoholExpected SignObserved ECCD! nm ("#)EntryPyridylAlcoholExpected SignObserved ECCD! nm ("#)\$h6578&'()*1';?CDEFG<,'
KLLI&0(8(&>-,&(?*@?&7.<7A8.830&)26,(?&4@,60@?&(?)-2-?7#&&123&3H43)830&
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7.<78,(83#&i3H8B&823&KLLI&78.0@&->&823&4@,60@?&(?)-2-?7&;(7&)-/0.)830#&&V7&823&8378&7.<78,(83&
4,-56030&KLLI&6/&23H(/37&(8&O&
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-200!-150!-100!-50!0!50!100!150!200!250!380!415!450!Mol CD !Wavelength (nm)
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)-/7603,30&(7&4-776<?3&)-/>-,93,7&8-&<6/0&;682&823&8;33:3,#&&i3H8B&(??&76H&,-8-93,7&->&823&
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,34,373/830&<@&823&+,33/&(/0&<?.3&(,,-;7&;682&823&?(<3?7&F$&(/0&F\B&,3743)A53?@#&&12-73&
)-/>-,93,7&82(8&4?()30&823&<6/06/+&+,-.47&4(,(??3?&7.)2&82(8&823&4-,42@,6/7&;-.?0&2(53&8-&

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->&823&4-,42@,6/&?637&6/&823&4?(/3&->&823&4(43,#&&123,3&(,3&/-&783,6)&6/e.3/)37&-/&8267&4-,42@,6/&

7-B&68&;6??&,39(6/&78(A)&6/&82(8&?-)(A-/#&&123&783,6)&067),696/(A-/&-)).,7&;682&F$#&&J-,&<-82&
)-94?3H37B&823&4-,42@,6/&F$&(44,-()237&823&2@0,-H@?&7.)2&82(8&823&4?(/3&->&823&4-,42@,6/&67&6/&
823&4?(/3&->&823&4(43,&<.8B&8267&4-,42@,6/&;6??&,-8(83&8-&,30.)3&6/83,()A-/7&;682&823&j&+,-.4#&&!/&

H*(B&823&4-,42@,6/&,-8(837&)-./83,)?-)*;673&,37.?A/+&6/&(/&-53,(??&)?-)*;673&23?6)68@&->&823&
4-,42@,6/7&>,-9&F$&8-&F\&(/0&(&4-76A53&KLLI&;-.?0&<3&3H43)830#&&123&-44-7683&(,,(/+393/8&67&
\\d3H43)830&>-,&
H*((
#&&123&4-,42@,6/B&F$B&
;6??&,-8(83&)?-)*;673&8-&4,-0.)3&(/&-53,(??&
)-./83,)?-)*;673&(,,(/+393/8&->&823&4-,42@,6/7&>,-9&F$&8-&F\&82.7&(&/3+(A53&KLLI&67&
3H43)830#&&c.)2&?6*3&;682&823&L\E&(/0&LdE&7.<7A8.830&_E(?*@?&4@,606/-?7B&823&)-94?3H&
H*(&;(7&
NNOHHRSorHROHA.1guacheA.2guacheZnP1P2ZnNHRHONHROHNHRHONHOHRNOHHRNROHHNROHHNHRHONHROHZnZnZnP1P2ZnZnZnP1P1P2P2B:A.1.aA.1.bA.1.cA.2.aA.2.bA.2.cC:R = alkylC.IC.IIA:\\g!"#$%&'()*+-,
&F,-4-730&9/39-/6)&>-,&_E(?*@?&7.<7A8.830&gE4@,60@?&(?)-2-?7#&&[2-;/&67&(/&
N#P&(?)-2-?#&&[33&83H8&>-,&823&038(6?30&3H4?(/(A-/#&&
3,'
u.()23&,-8-93,7&(<-.8&823&
4@,606/3ELgv_E)(,<-/&<-/0#&&
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H,&123,3&(,3&8;-&4-776<?3&
)-94?3H37&;682&823&8;33:3,&(/0&823&9-78&>(5-,30&4@,606/-?&,-8-93,7#&&
H*((
&67&9-78&?6*3?@&
0.3&8-&?3(78&783,6)&6/83,()A-/7#3?696/(830&(7&823&>(5-,30&)-94?3H&0.3&8-&4-776<?3&6/83,()A-/7&<38;33/&823&j&+,-.4&(/0&?6/*3,&
->&823&8;33:3,#&&123,3>-,3B&
H*((
&67&82-.+28&8-&<3&823&>(5-,30&)-94?3H&(/0&(&/3+(A53&KLLI&
;-.?0&<3&3H43)830&>-,&823&N
#P&(?)-2-?#&&J.,823,9-,3B&823&N
"P&(?)-2-?&67&3H43)830&8-&4,-5603&(&

4-76A53&76+/(?#&&1267&4,306)A-/&>,-9&823&<6/06/+&9-03?&9(8)237&;3??&;682&823&-<73,530&KLLI&

>-,&823&LgE_E(?*@?&4@,606/-?7#&123&-823,&(?*@?&7.<7A8.830&4@,606/-?7&N(8&823&`E&(/0&wE)(,<-/7P&060&/-8&>-??-;&823&
9/39-/6)&378(<?67230&>-,&823&_E(?*@?&4@,606/-?7&36823,#&&123&`E&(/0&wE7.<7A8.830&4@,606/-?7&2(53&

(&?(,+3,&03+,33&->&>,330-9B&;26)2&9.78&<3&)-/7603,30&8-&0353?-4&(&9/39-/6)&>-,&82373&
)-94?3H37#&&J6+.,3&!"#$d&7.99(,6:37&823&4,-4-730&<6/06/+&9-03?7&>-,&823&`E&(/0&wE7.<7A8.830&
4@,606/-?7#&&J6,78B&)-/7603,&823&`E(?*@?&4@,606/-?&NJ6+.,3&!"#$d&VP#&&123&,-8(A-/&(<-.8&823&
4@,606/3E
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)3/83,&(,3&3H43)830&6/&8267&)-/>-,9(A-/#&&i3H8B&823&,-8-93,7&->&823&_E)(,<-/&8-&`E)(,<-/&<-/0&
;3,3&)-/7603,30#&&V+(6/B&-/?@&78(++3,30&)-/>-,9(A-/7&;3,3&)-/7603,30&(7&82373&(,3&?-;3,&6/&

3/3,+@&82(/&823&3)?64730&)-/>-,9(A-/7#&&123,3&(,3&82,33&,-8-93,7&->&8267&<-/0#&&J-,&8;-&->&823&
,-8-93,7B&
3*-*7&(/0&
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?-)(830&-/&823&7(93&>()3&->&823&9-?3).?3#&&12.7&823&4-,42@,6/7&;-.?0&(44,-()2&823&<6/06/+&
76837&>,-9&823&7(93&>()3B&(7&6/06)(830&<@&823&+,33/&(/0&<?.3&(,,-;7#&&V7&067).7730&(<-53B&8267&67&
./>(5-,(<?3&(/0&./?6*3?@&0.3&8-&823&76:3&->&823&4-,42@,6/#&&123,3>-,3B&823&
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3*\\TNROHHRNNHRHHHRHOHNROHHRPyHHHORHPyHHHOHRPyHHRHOHZnP1P2ZnZnZnP1P2RZnZnNOHRHRZnP1P2ZnP1P2A: !-alkyl pyridinolB: "-alkyl pyridinolA.1eclipsedA.2guacheNHHOHRHRNHHHRHOHHA.2.aA.2.bA.2.cP2P1P1P1P2P2R = alkylR = alkylNHHRHOHCH2PyHHOHRHNHHOHRHR!A.2A.2.a\\]!"#$%&')(*+.,'
'6/06/+&9/39-/6)&>-,&
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`E)(,<-/&<-/0#&&123&(44,-()2&->&823&4-,42@,6/7&67&6/06)(830&<@&823&
+,33/&(/0&<?.3&(,,-;7#&&'6/06/+&;682&823&9-78&>(5-,30&)-/>-,93,&;-.?0&+3/3,(83&(&
4-76A53&KLLI#&&
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)-94?3H&(7&9-78&>(5-,30#&&1267&;-.?0&4,-5603&(&4-76A53&KLLI&76+/(?#-*5&i3;9(/&4,-^3)A-/7&+6537&823&82,33E
0693/76-/(?&,34,373/8(A-/&->&823&(?)-2-?&;26)2&67&
82-.+28&8-&<3&823&)-/>-,9(A-/&82(8&67&4,3>3,,30&;23/&<-./0&8-&823&8;33:3,#&&V7&<3>-,3B&F$&
(44,-()237&823&>,-/8&->&823&9-?3).?3&;682&823&4?(/3&->&823&4-,42@,6/&6/&823&4?(/3&->&823&4(43,&
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<()*&>()3&->&823&9-?3).?3&(+(6/&;682&823&4?(/3&->&823&4-,42@,6/&6/&823&4?(/3&->&823&4(43,#&&1267&
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->&823&4-,42@,6/7&>,-9&F$&8-&F\#&&V&)?-)*;673&23?6)68@&;-.?0&+3/3,(83&(&4-76A53&KLLI&<676+/(83&
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23?6)68@&->&823&4-,42@,6/7&>,-9&F$&8-&F\&(/0&(&4-76A53&KLLI&76+/(?&67&4,306)830#&&V+(6/B&8267&
(+,337&;682&823&-<73,530&KLLI#&1(<?3&!"#h&7.99(,6:37&823&KLLI&0(8(&-<73,530&>-,&823&(,-9(A)&7.<7A8.830&4@,60@?&

(?)-2-?#&&t/>-,8./(83?@B&823&(?)-2-?7&(8&823&L\E4-76A-/&->&823&4@,606/3&4,-56030&;3(*&-,&/-&
KLLI&76+/(?&&123&93768@?&7.<7A8.830&(?)-2-?7B&
()*+"
B&+3/3,(830&/-67@&KLLI&76+/(?7&->&-44-7683&
76+/&(/0&3M.(?&6/83/768@#&&123&;3(*&-,&./-<73,5(<?3&KLLI&>-,&82373&(,-9(A)&7.<78,(837&67&?6*3?@&
0.3&8-&823&6/),3(730&783,6)7&(,-./0&823&(?)-2-?&(7&(,@?&7.<7A8.3/87&(,3&+3/3,(??@&?(,+3,&82(/&
(?*@?&7.<7A8.3/87#&&123&V&5(?.3&->&(/&67-4,-4@?&7.<7A8.3/8&67&\#$T&*)(?v9-?&(/0&823&423/@?&
+,-.4&67&d#O&*)(?v9-?#&&123,3>-,3B&823&?(,+3&7.<7A8.3/8&)-.?0&<3&6/26<6A/+&<6/06/+&;682&823&
\\hNOHNOHNOH(R)-IV.1h
90% ee(R)-IV.1i
75% eeNOH(R)-IV.1k
90% ee(R)-IV.1l
80% eeNOH(R)-IV.1j
90% eeEntryPyridylAlcoholExpected SignObserved ECCD! nm ("#)EntryPyridylAlcoholExpected SignObserved ECCD! nm ("#)13254NOH(S)-IV.1h
> 95% eeNOH(S)-IV.1i
> 95% ee687109NOH(S)-IV.1j
95% eeNOH(S)-IV.1k
95% eeNOH(S)-IV.1l
> 95% ee422 (+24)415 (-14)A = +38423 (-18)414 (+16)A = -34NO ECCD426 (-149)413 (+93)A = -242426 (+106)413 (-40)A = +146426 (+239)414 (-121)A = +360NO ECCDNO ECCDNO ECCD426 (-479)414 (+296)A = -775\\Q6578&'()*2,'
KLLI&0(8(&>-,&823&(,@?&7.<7A8.830&4@,60@?&(?)-2-?7#&&123&3H43)830&76+/&67&
<(730&-/&823&9/39-/6)7&0353?-430&>-,&823&(?*@?&4@,60@?&(?)-2-?7#&&V??&93(7.,393/87%&
23H(/37B&O&
.LB&\&sc&8;33:3,B&$&3M.65(?3/87&->&7.<78,(83#&(%&]O&3M.65(?3/87&->&7.<78,(83#
2@0,-H@?B&>-,9(A-/&->&823&
8;33:3,E7.<78,(83&)-94?3H&(/0&+3/3,(A-/&->&823&KLLI&76+/(?#&&&123&LdE&(/0&LgE&7.<7A8.830&(?)-2-?7&060&2-;353,B&4,-5603&KLLI&76+/(?7&N1(<?3&!"#hP#&&
12373&(,3&>(6,?@&6/83/73&76+/(?7&(,3&;3,3&6/6A(??@&7.,4,676/+&<36/+&82(8&823&L\E7.<7A8.830&
(?)-2-?7&>(6?30#&&123&7.))377&->&82373&(?)-2-?7&67&82-.+28&8-&<3&823&,37.?8&->&9-56/+&823&2@0,-H@?&

<6/06/+&7683&(;(@&>,-9&823&4@,606/3&/68,-+3/&<6/06/+&7683#&&1267&)-.?0&,3?6353&)-/+37A-/&(8&823&
<6/06/+&76837&(/0&4,-9-83&>-,9(A-/&->&823&8;33:3,E7.<78,(83&)-94?3H&353/&;682&823&?(,+3,&
(,-9(A)&7.<7A8.3/87#&&!>&823&9/39-/6)7&0353?-430&>-,&823&(?*@?&7.<7A8.830&4@,606/-?7&67&

(44?630&8-&823&(,-9(A)&4@,606/-?7B&823&KLLI&->&$ENgE4@,60@?P423/@?9382(/-?&N
()*+8
PB&)-,,3?(837&
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(?)-2-?7B&823&N
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7;68)2&76+/#&&123&9/39-/6)&0353?-430&4?()37&823&?(,+378&7.<7A8.3/8&6/&823&?3(78&783,6)(??@&
)-/+37830&?-)(A-/#&&123&?(,+3&(,-9(A)&7.<7A8.3/87&72-.?0&(?7-&>(5-,&8267&4-76A-/#&&12.7B&823&

9/39-/6)&>-,&823&(?*@?&4@,60@?&(?)-2-?7&72-.?0&(?7-&<3&5(?60&>-,&823&(,@?&4@,60@?&(?)-2-?7#&1-&3/7.,3&82(8&823&<378&)-/06A-/7&>-,&KLLI&;3,3&6/&.73&N23H(/37&(8&O&
.LPB&(&7-?53/8&(/0&
83943,(8.,3&78.0@&;(7&)-/0.)830&;682&N
"PEN\E4@,60@?P93768@?9382(/-?&N
()*+"
PB&823&,37.?87&(,3&
7.99(,6:30&6/&1(<?3&!"#Q#&&X-;3,6/+&823&83943,(8.,3&8-&E$O&
.L&6/&23H(/37&060&694,-53&823&
76+/(?B&<.8&-/?@&7?6+28?@#&&S(,96/+&8-&$O&
.L&-,&,--9&83943,(8.,3&6/&23H(/37&+(53&/-&
694,-5393/8&->&(94?68.03#&&S23/&9382@?)@)?-23H(/3&;(7&.730&823&KLLI&(94?68.03&;(7&
)-94(,(<?3&8-&23H(/37#&&1-?.3/3&(/0&LU
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)2-73/&>-,&7.68(<?3&>-,&823&KLLI&78.0@#&&J.,823,9-,3B&823&76+/&->&823&KLLI&,39(6/30&)-/78(/8&

./03,&82373&(?83,30&)-/06A-/7#\\R&!/&(006A-/&8-&823&KLLI&78.0@B&(&t"E"67&(/(?@767&->&3()2&)-94?3H&;(7&(?7-&)-/0.)830&
@63?06/+&Y-<m7&4?-8&(/(?@767&(/0&>-,&)(?).?(A-/&->&823&8;33:3,E7.<78,(83&<6/06/+&)-/78(/87#&&Y-<m7&
4?-8&(/(?@767&,353(?30&823&>-,9(A-/&->&$%$&)-94?3H37&N733&3H43,693/8(?P#&&123&<6/06/+&)-/78(/8&
>-,&823&L\E7.<7A8.830&_E(?*@?&4@,606/-?7&3H26<6830&<6/06/+&)-/78(/87&6/&823&-,03,&->&$O
&&c'!&N1(<?3&!"#RP#&&123&<6/06/+&)-/78(/87&>-,&
()*+J'
(/0&
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&(,3&+,3(83,&82(/&$OE>-?0&?(,+3,&82(/&
82-73&>-,&
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#&&123&A+283,&<6/06/+&)-/78(/87&23?4&8-&3H4?(6/&823&?(,+3,&KLLI&76+/(?7&
>-,&82373&7.<78,(837#&&!8&;(7&2@4-82376:30&82(8&9-56/+&823&2@0,-H@?&)3/83,&(;(@&>,-9&823&

4@,606/3&/68,-+3/&;-.?0&4,-9-83&<6/06/+&;682&823&8;33:3,&<@&,3?6356/+&783,6)&)-/+37A-/&
NOH427 (+43) 419 (-30) A = +73SolventECCDEntryTemp
123450 ¡C-10 ¡C10 ¡Crt0 ¡ChexaneshexaneshexaneshexanesMCH426 (+67) 416 (-40) A = +107426 (+43) 419 (-22) A = +65425 (+31) 417 (-20) A = +51427 (+53) 416 (-37) A = +90(R)-IV.1i
60 equiv670 ¡C0 ¡CtolueneNoECCDNoECCDCH2Cl2SolventECCDEntryTemp
\dO6578&'()*:,
&[-?53/8&(/0&83943,(8.,3&7),33/&;682&;8<9()*+"
#&&\&sc&8;33:3,#(,-./0&823&<6/06/+&76837#&&
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)-,,-<-,(83&8267&2@4-823767#&&&123&4--,&KLLI&,37.?87&>-,&L\E7.<7A8.830&_E(,@?&4@,606/-?7&;(7&82-.+28&8-&<3&0.3&8-&
6/),3(730&783,6)&)-/+37A-/&82(8&;-.?0&6/26<68&<6/06/+&;682&823&4-,42@,6/&8;33:3,#&&V+(6/B&823&

<6/06/+&)-/78(/8&>-,&
()*+@
&NN\E4@,60@?PE423/@?9382(/-?B&y
/&z&dBOOO&c
'!P&)-/G,97&8267&
Nn-C5H12OH(R)-IV.3g
Nn-C5H12OH(S)-IV.3a
Nn-C5H12OH(S)-IV.3f
NOH(S)-IV.1h
NOH(S)-IV.1k
NOH(S)-IV.1l
7677400 ± 13339000.999261244200 ± 1261000.994242924 ± 2060.996814093400 ± 5196700.9992613224 ± 7080.998294494100 ± 10803000.99587123456EntryEntrySubstrateSubstrateKa ± error (M-1)R2Ka ± error (M-1)R2\d$6578&'()*=,'
'6/06/+&)-/78(/87&>-,&LQED/E1FJFE1;33:3,&;682&4@,60@?&(?)-2-?7#&&'6/06/+&
)-/78(/87&>-,&L\E7.<7A8.830&4@,60@?&(?)-2-?7&(,3&79(??3,&82(/&823&LdE&(/0&LgE
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1:&N1(<?3&!"#$OP#&&123&,(A-/(?3&>-,&823&-<73,530&KLLI&76+/&67&7.99(,6:30&6/&J6+.,3&!"#$T#&&!8&67&
7.,4,676/+&82(8&82373&(?)-2-?7&+3/3,(83&(/&KLLI&76+/(?#&&J-,&823&4@,606/3&<(730&(?)-2-?7B&823,3&67&
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\d\EntryChiralGuestObserved ECCD! nm ("#)EntryChiralGuestObserved ECCD! nm ("#)MeNOHMeNOH(S)-IV.25
(R)-IV.25
NONNONOONHHHHNOON13245423 (-64)413 (+47)A = -111
b424 (+77)413 (-44)A = +121b432 (+309)425 (-597)416 (+190)d425 (-75)415 (+70)A = -145c429 (+2223)419 (-1408)A = +3631dIV.30
IV.28
IV.29
TsNOHIV.27
423 (+238)413 (-135)A = +373c6OOHOSOn-C5H11OHOHOHNo ECCDaNo ECCDaNo ECCDaNo ECCDa(R)-IV.21
(R)-IV.23
(R)-IV.24
(S)-IV.26
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88% ee421 (-147)412 (+ 88)A = -235V.7
88% ee421 (-520)414 (+353)A = -873V.8
98% ee421 (-650)415 (+420)A = -1070V.9
88% ee422 (+294)413 (-159)A = +435V.10
88% ee422 (+647)413 (-300)A = +947V.11
21% ee422 (+67)414 (-34)A = +101OO= MEDAMNaL!"#$%&'()6+
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NRHHONHR'NRHHR'P1P2ZnP2P1C5-Zn-TPFP-TzRRPGPGZnZnZnNHOP2P1ZnZnNaN!"#$%&'()*@+
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'92/34%@278%'.%A
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+M5+,73(73/M%&'()M'12+2/2.3%'92/34%
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%&'()%'12+2/2.3%'92/34%+3V-2+3/%/3>3?,593.7%,E%'%435'+'73%9.39,.2(%'4%78343%'+3%/2'473+3,93+4%,E%

783%*$)M'12+2/2.3%'92/34"%%%B2*-+3%!"#N%4-99'+2134%783%^bbR%+34-?74%E,+%783%
%&'()M'12+2/2.3%'92/34"%%D824%'.'?;424%
@'4%'%(,9:2.3/%3[,+7%@278%R+"%`2"%%B2*-+3%!"#a%24%435'+'73/%2.7,%783%4-:47+'734%'.'?;13/%:;%R+"%
`2%A0C%'./%78,43%'.'?;13/%'4%'%5'+7%,E%9;%47-/234%A&C"%%h.%7,7'?%783+3%@3+3%#H%
%&'()M'12+2/2.3%'92/34%47-/23/"%%FE%78343%#H%4-:47+'734<%E,-+%,E%783%'12+2/2.34%/2/%.,7%E,??,@%783%*3.3+'?%7+3./%

,:43+>3/%A
()*6
<%()*5
<%(),5
%'./%
()-@
C"%%B,+%9,47%4-:47+'734<%^bbR%42*.'?%@'4%,:43+>3/%@278%'4%
?2Y?3%'4%L"a%3V-2>'?3.74%,E%4-:47+'73%'./%783%7@3313+%@'4%7,?3+'.7%,E%:,78%'+;?%'./%'?);?%*+,-54%
'7%783%bN%('+:,.%'4%@3??%'4%783%'92/3%3./%,E%783%4-:47+'734"%%h.%*3.3+'?<%783%Aa
!<%N
#C%(,.G*-+3/%
'12+2/2.3%'92/34%*3.3+'73/%.3*'=>3%^bbR%'./%783%Aa
#<%N
!C%'12+2/2.3%'92/34%5+,>2/3/%5,42=>3%
^bbR"%%%%%%%NaJNMEDAMHNONMEDAMHNONMEDAMHNONMEDAMHNONMEDAMHNONMEDAMHNOClMeOO2NBrFV.12
96% ee423 (-26)415 (+31)A = -57V.15
85% ee423 (-173)414 (+115)
A = -288V.16
80% ee423 (-56)417 (+71)A = -217V.13
90% ee423 (-91)417 (+82)A = -173V.14
93% ee422 (-55)415 (+33)A = -88V.17
94% ee423 (-113)
415 (+85)A = -198NMEDAMHNONMEDAMHNONMEDAMHNOBrV.20
80% ee424 (-19)417 (+27)A = -46V.21
91% ee423 (-112)
417 (+108)A = -220V.22
99% ee423 (-71)416 (+74)A = -145NMEDAMHNONMEDAMHNOCF3ClV.18
78% ee424 (+56)415 (-77)405 (+32)V.19
92% ee423 (-43)417 (+78)406 (-27)AB23OMeNaH!"#$%&'()*-
$%^bbR%'.'?;424%,E%
%&'()M'12+2/2.3%'92/34"%%P-:47+'734%2.%:?-3%/3>2'73%E+,9%
783%*3.3+'?%7+3./"%%0??%93'4-+393.74$%a%kc%7@3313+<%836'.34<%L%
-b<%I%3V-2>'?3.74%,E%
4-:47+'73"%'$%aL%3V-2>'?3.74%,E%4-:47+'73"%%.+%0.'?;13/%:;%R+"%`2"%04%:3E,+3<%m!M!24%'.'?;424%@'4%'?4,%(,./-(73/%E,+%78343%4-:47+'734"%%B,+%9,47%
4-:47+'734<%783+3%@'4%'55+,629'73?;%'%I%.9%482U%,E%783%P,+37%:'./%@82(8%2./2('734%78'7%'%#$#%
7@3313+M4-:47+'73%(,95?36%8'/%E,+93/r%B2*-+3%!"#g%&%5+,>2/34%783%m!M!24%=7+'=,.%@278%
(),*
"%%
NMEDAMHNONMEDAMHNONMEDAMHNONMEDAMHNONMEDAMHNOC14H29C14H29C14H29NMEDAMHNOV.30
32% ee423 (-214)416 (+142)A = -356V.25
98% ee422 (+59)416 (-35)A = +94V.26
98% ee424 (+47)418 (-33)A = +80V.27
57% ee423 (+204)417 (-139)A = +343aNMEDAMHNOV.28
93% ee424 (+50)417 (-64)A = +114
NMEDAMHNOV.23
94% ee422 (-50)415 (+44)A = -94aMeOV.24
82% ee423 (-52)416 (+62)A = -114
V.29
87% ee423 (-121)416 (+39)A = -160BNNL!"#$%&'()*-'89:;<=>?
-140!-90!-40!10!60!110
!Mol CD!Wavelength (nm)
!background!2.5 equiv!5 equiv!7.5 equiv!10 equiv!15 equiv!20 equiv!30 equiv!3804004204400!0.1!0.2!0.3!0.4!0.5!0.6!0.7!0.8!0.9!1!370!390!410!430!450!Absorbance!Wavelength (nm)
!background!2 equiv!4 equiv!6 equiv!8 equiv!10 equiv!15 equiv!20 equiv!NN#g##%.9
g#K%.9
/.g#O%.9
gaN%.9
!"#$%&'()*0+
%0.'?;424%,E%783%bIMf.MD_B_MD1%'./%
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.+%^bbR%=7+'=,.%a%kc%D1<%
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-b"%%/+%m!M!24%=7+'=,.%#%kc%D1<%836'.34<%+,,9%73953+'7-+3"
&2./2.*%
(,.47'.7%/373+92.'=,.%
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'(),*
%3?-(2/'73/%'%:2./2.*%(,.47'.7%,E%#"K%6%#L
)%c"!%@82(8%24%,E%4292?'+%9'*.27-/3%'4%783%
*$)M'12+2/2.3%'92/34"%%&32.*%78'7%'??%,E%783%'12+2/2.3%
'92/34%8'>3%4292?'+%:2./2.*%E-.(=,.'?2=34<%
+Mc^R0c%5+,73(73/%.27+,*3.%'./%'.%'92/3<%27%24%
.,7%4-+5+242.*%78'7%'??%,E%78343%4-:47+'734%8'>3%4292?'+%:2./2.*%'i.2=34%E,+%783%7@3313+"%%%D83%:2./2.*%9,/3?%E,+%78343%
%&'()M'12+2/2.3%'92/34%24%4-99'+213/%2.%B2*-+3%!"#I"%%04%
@278%783%
*$)M'12+2/2.3%'92/34<%783%?,('=,.%,E%783%.27+,*3.%5+,73(=.*%*+,-5%24%783%?'+*347%E'(7,+%
*,>3+.2.*%783%:2./2.*%'./%7+'.4E3+%,E%(82+'?27;%E+,9%783%'12+2/2.3%7,%783%7@3313+"%%h7%24%'44-93/%
78'7%5;+'92/'?21'=,.%,E%783%.27+,*3.%@2??%:3%4-(8%78'7%783%5+,73(=.*%*+,-5%24%
).(%7,%783%'92/3%
NNa4!"#$%&'()*0'89:;<=>?+
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E-.(=,.'?27;%'4%783%45
$%('+:,.%,E%783%'92/3%('+:,.;?%'7%('+:,.%a%,E%783%'12+2/2.3%48,-?/%:3%
473+2('??;%49'??3+%78'.%783%e%*+,-5%'7%('+:,.%N%,E%783%'12+2/2.3"%%B-+783+9,+3<%7824%(,.E,+9'=,.%
,E%783%.27+,*3.%@2??%E,+(3%783%.27+,*3.%?,.3%5'2+%3?3(7+,.4%7,%783%,55,4273%E'(3%'4%783%'12+2/2.3"%%
D824%5?'(34%783%:2./2.*%E-.(=,.'?2=34%
'(-%7,%,.3%'.,783+%@82(8%24%5+3E3++3/%E,+%E,+9'=,.%,E%
783%8,47M*-347%(,95?36%'4%7824%@2??%427-'73%783%5,+58;+2.4%
'(-%7,%,.3%'.,783+"%%Z278%783%
P1P2P2P1NHRHONHR'NHRHONHR'C5-Zn-TPFP-TzSRNROHNR'ZnZnRSPGPGZnZnPGP2P1ZnZnNNN!"#$%&'()*1+
%^bbR%9,/3?%E,+%
+M5+,73(73/M%&'()M'12+2/2.3%'92/34"%%0.%A
a#<%N
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)%%_;+'92/'?21'=,.%,E%783%.27+,*3.%E'>,+4%5?'(393.7%,E%783%
5+,73(=.*%*+,-5%7,%783%,55,4273%E'(3%,E%783%'12+2/2.3%4-:4=7-3.74"%%c2.2921'=,.%,E%
473+2(%E'(7,+4%+34-?74%2.%783%83?2(27;%,E%783%5,+58;+2.4%'./%783%3653(73/%42*.%,E%783%^bbR%
42*.'?"'44-95=,.%78'7%7824%24%783%5+3E3++3/%(,.E,+9'=,.%
,E%783%'12+2/2.3<%:2./2.*%,E%783%5,+58;+2.4%
,((-+4%2.%'%9'..3+%7,%92.29213%473+2(%2.73+'(=,.4%:37@33.%783%5,+58;+2.4%'./%783%'12+2/2.3"%%
D83%5,+58;+2.%78'7%:2./4%@278%783%'92/3%('+:,.;?%'55+,'(834%E+,9%783%4'93%E'(3%,E%783%
'12+2/2.3%'4%783%5+,73(=.*%*+,-5%'./%+,7'734%'@';%E+,9%783%'12+2/2.3"%%D83%43(,./%5,+58;+2.<%

_a<%:2./4%7,%783%,55,4273%E'(3%,E%783%'12+2/2.3%7,%92.29213%5,+58;+2.M5,+58;+2.%2.73+'(=,.4"%%
D824%5,+58;+2.%@2??%+,7'73%7,@'+/%_#%7,%92.29213%473+2(%2.73+'(=,.%@278%783%'12+2/2.3%
4-:4=7-3.7"%%F>3+'??<%
7824%5+3/2(74%'%(?,()@243%'++'.*393.7%,E%5,+58;+2.4%'./%'%5,42=>3%^bbR%
:242*.'73%(-+>3%E,+%A
a#<%N
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7824%9,/3?%5+3/2(74%'%
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m!M!24%=7+'=,."%%D83%&mR0c%5+,73(=.*%*+,-5%24%?'+*3+%78'.%783%c^R0c%5+,73(=.*%*+,-5%

783+3E,+3<%27%@'4%'.=(25'73/%78'7%783%5+,73(=.*%*+,-5%,E%78343%4-:47+'734%(,-?/%2.82:27%:2./2.*%

'./%@,-?/%7347%783%?29274%,E%783%bIMf.MD_B_MD1"%%0??%,E%78343%4-:47+'734%5+,>2/3/%@3')%'./%.,24;%
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4-:47+'73%@'4%.3(344'+;%7,%,:43+>3%^bbR%42*.'?%@82(8%24%'.%2./2('=,.%783%'12+2/2.34%'+3%@3')?;%
:2./2.*%4-:47+'734"%%D83%:2./2.*%(,.47'.7%E,+%4-:47+'73%
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"!.@82(8%24%#LME,?/%49'??3+%78'.%783%c^R0c%5+,73(73/%'12+2/2.34"%%h7%24%8;5,7834213/%78'7%783%@3')%

:2./2.*%,E%783%4-:47+'73%?3'/4%7,%783%2.(,.42473.7%^bbR%+34-?74"%%D83%5,,+%:2./2.*%,E%783%
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'>3+'*3%7,*3783+%2.7,%783%@3')%42*.'?4"%%D83+3E,+3<%/373+92.'=,.%,E%':4,?-73%(,.G*-+'=,.%E,+%

&mR0c%5+,73(73/%'12+2/2.3%'92/34%('..,7%:3%'(823>3/%@278%bIMf.MD_B_MD1"NNg!"g$%b,.(?-42,.4%,.%783%012+2/2.3%092/34%^bbR%'./%m!M!24%'.'?;424%,E%426%
*$)M'12+2/2.3%'92/34%'./%#H%
%&'()M'12+2/2.3%'92/34<%
,:7'2.3/%E+,9%783%Z-?[%?':<%'??,@3/%E,+%783%/3>3?,593.7%,E%9.39,.2(4%E,+%:,78%(?'4434%,E%

'12+2/2.34"%%D8343%4-:47+'734%3682:27%4292?'+%:2./2.*%'i.2=34%E,+%783%5,+58;+2.%7@3313+%A#L
)%c"!C%'./%^bbR%42*.'?4%'+3%,:43+>3/%@278%'4%?2Y?3%'4%L"a%3V-2>'?3.74%,E%783%'12+2/2.3<%'7%
(,.(3.7+'=,.4%,E%#L
"*%c"%%B,+%:,78%(?'4434%,E%4-:47+'734<%783%5;+'92/'?21'=,.%,E%783%.27+,*3.%
/2(7'734%783%?,('=,.%,E%783%5+,73(=.*%*+,-5%,.%783%.27+,*3.%,E%783%'12+2/2.3"%%D83%5+3E3++3/%
NBUDAMHNONBUDAMHNONBUDAMHNOV.31
80% eeNo ECCDV.32
89% ee422 (-10)413 (+13)A = -22(60 equiv)V.33
88% ee424 (-12)415 (+29)A = -41(200 equiv)NBUDAMHNOV.35
70% ee423 (-12)415 (+19)A = -31(100 equiv)NBUDAMHNOV.34
83% ee423 (+9)416 (-12)A = +21(400 equiv)OOBUDAMNNI!"#$%&'()*2+
%P-99'+;%,E%783%^bbR%+34-?74%E,+%783%&mR0c%5+,73(73/%
%&'()M'12+2/2.3%'92/34"%%0??%93'4-+393.74$%a%kc%7@3313+<%836'.34<%L%
-b"5;+'92/'?21'=,.%24%78'7%@82(8%427-'734%783%5+,73(=.*%*+,-5%,E%783%.27+,*3.%7,%783%4'93%E'(3%,E%
783%'12+2/2.3%@278%783%49'??347%4-:4=7-3.74%,.%783%'12+2/2.3%('+:,.4"%%F.(3%783%5+3E3++3/%
5;+'92/'?21'=,.%,E%783%.27+,*3.%24%/373+92.3/<%:2./2.*%,E%783%7@3313+<%83?2(27;%,E%783%
5,+58;+2.4%'./%783%42*.%,E%783%^bbR%42*.'?%@'4%5+3/2(73/"%%D824%4;4739%24%7,?3+'.7%,E%'+;?%'./%

'?);?%4-:4=7-3.74%'7%bN%'./%783%'92/3%:-7%24%?29273/%:;%783%4213%,E%783%.27+,*3.%5+,73(=.*%*+,-5%
'4%/39,.47+'73/%@278%783%&mR0c%5+,73(73/%'12+2/2.34"%%h7%24%78,-*87%78'7%7824%?'+*3%5+,73(=.*%
*+,-5%2.82:274%4-:47+'73%:2./2.*%'./%?3'/4%7,%@3')%'./%2.(,.42473.7%^bbR%42*.'?4"!"I$%^bbR%P7-/;%,E%*$)M^5,6;%092/34
'c,47%+3(3.7?;<%939:3+4%,E%783%Z-?[%?':%/39,.47+'73/%78'7%
*$)M35,6;%'92/34%('.%:3%
4;.7834213/%-42.*%'%4292?'+%5+,7,(,?%E,+%783%4;.783424%,E%783%
*$)M'12+2/2.3%'92/34"%%h.%7,7'?<%#O%(24M
35,6;%'92/34%@3+3%*3.3+,-4?;%/,.'73/%E,+%^bbR%'./%m!M!24%'.'?;424"%%04%/24(-443/%':,>3<%'.%

^bbR%9.39,.2(%@'4%/3>3?,53/%E,+%783%/373+92.'=,.%,E%':4,?-73%(,.G*-+'=,.%,E%35,6;%

'?(,8,?4"%%D824%47-/;%5+,>3/%78'7%'.%35,62/3%,6;*3.%24%'%4-27':?3%:2./2.*%E-.(=,.'?27;%E,+%783%
3?3(7+,.%/3G(23.7%bIMf.MD_B_MD1"
%$%%0//2=,.'??;<%E+,9%783%^bbR%47-/234%,E%/3+2>'=13/%
4-:47+'734<%27%@'4%).,@.%78'7%'92/3%E-.(=,.'?2=34%(,-?/%'?4,%5'+=(25'73%2.%'%:2./2.*%

2.73+'(=,.%@278%783%5,+58;+2.%7@3313+4"
%%,%)%%D83+3E,+3<%27%@'4%8;5,7834213/%78'7%783%35,6;%
'92/34%@,-?/%:2./%@278%bIMf.MD_B_MD1%78+,-*8%:2./2.*%2.73+'(=,.4%@278%783%35,62/3%,6;*3.%

'./%783%,6;*3.%,E%783%'92/3%('+:,.;?"%%%B,+7-.'73?;<%'??%#O%4-:47+'734%/2/%5+,/-(3%'.%^bbR%42*.'?%AB2*-+3%!"#OC"%%h.2='??;<%783%

4-:47+'734%@3+3%'.'?;13/%@278%bIMf.MD_B_MD1%'7%L%
-b%2.%836'.34%E,??,@2.*%783%+35,+73/%5+,7,(,?%
E,+%783%35,6;%'?(,8,?4"
%$%%m./3+%78343%(,./2=,.4<%783+3%@3+3%43>3+'?%4-:47+'734%78'7%5+,>2/3/%
NNKOHNOnBuOHNOnBuBrOHNOnBuBrFOHNOnBuOHNOOHNOV.36
92% eeV.37
80% eeV.39
62% eeV.38
92% eeV.45
55% ee423nm (+200)410nm (-101)A = +301422nm (+119)
411nm 
(-70)A = +189423nm (+34)   411nm 
(-19)A = +53150 equiv424nm (+48)412nm (-48)A = +96424nm (+44)411nm 
(-42)A = +86100 equivC8H17424nm (+673)   412nm (-436)A = +1109
V.40
90% eeOHNOnBuNCOHNOnBuO2NOHNOnBuBrOHNOnBuOHNOClV.41
99% eeV.43
96% eeV.44
92% eeV.46
52% eeV.42
96% ee435nm (-18)423nm (+187)   411nm 
(-73)434nm (-32)  422nm (+32) A = -64 150 equivTrisignate 
above 150 equiv435nm (-12)423nm (+170)   411nm 
(-66)435nm (-5)423nm (+69)  411nm 
(-17)435nm (-15)423nm (+113) 
  412nm (-33)423nm (+264)410nm (-135)A = +399424nm (+151)412nm (-61)A = +212424nm (+111)
411nm 
(-55)A = +16650 equiv423nm (+30)   411nm 
(-20)A = +50400 equiv423nm (+387)   411nm 
(-209)A = +596423nm (+324)   411nm 
(-137)A = +461423nm (+209)   411nm 
(-91)A = +300423nm (+338)   411nm 
(-154)A = +492423nm (+67)   411nm 
(-33)A = +100 300 equiv423nm (+98)413nm (-59)A = +157424nm (+621)411nm 
(-404)A = +1025NNO!"#$%&'()*3+
%P-99'+;%,E%783%^bbR%+34-?74%E,+%
*$)M35,6;%'92/34"%%0??%93'4-+393.74$%a%
kc%7@3313+<%836'.34<%L%
-b%A:?'()C%,+%+,,9%73953+'7-+3%A:?-3C<%gL%3V-2>'?3.74%,E%
4-:47+'73%-.?344%,783+@243%.,73/"7+242*.'73<%@3')%,+%.,24;%^bbR%42*.'?4"%
%B2*-+3%!"#J%
0%5+,>2/34%'.%,>3+?';%,E%783%^bbR%
(,./2=,.4%4(+33.3/%E,+%4-:47+'73%
()00
"%%D,%295+,>3%783%^bbR%42*.'?4<%'%^bbR%=7+'=,.%,E%f.MbNM
D_B_MD1%'./%f.MbJMD_B_MD1%@278%
()00
%@'4%(,./-(73/"%%D8343%7@3313+4%@3+3%,5=9'?%E,+%,783+%
4-:47+'734%'./%27%@'4%8;5,7834213/%78'7%53+8'54%783%bIMf.MD_B_MD1%@'4%.,7%783%2/3'?%7@3313+%
,E%783%35,6;%'92/34"%%^'(8%,E%783%78+33%7@3313+4%-43/%5+,>2/3/%(,95?36%^bbR%42*.'?4%@278%
53')4%'7%'55+,629'73?;%gNI%.9<%gag%.9%'./%g#a%.9"%%D8343%(,95?36%42*.'?4%4-**347%78'7%783%
8,47M*-347%(,95?36%24%4'95?2.*%'%.-9:3+%,E%^bbR%'(=>3%(,95?3634"%%P-99'=,.%,E%783%^bbR%
OHNOnBuMeOHNOnBuMeOOHNOnBuOOOHNOnBuMeV.52
90% eeOHNOnBuBrV.47
99% ee423nm (+262)412nm (-170)A = +432423nm (-302)412nm (+134)A = -436423nm (-231)   411nm 
(+131)A = -362423nm (-205)   412nm (+121)A = -326424nm (-37)412nm (+44)A = -81V.48
97% eeV.51
80% eeV.49
99% eeOHNOnBu434nm (+45)423nm (-139)  412nm (+38)V.50
98% ee423nm (-353)   411nm 
(+203)A = -556423nm (-233)   412nm (+131)A = -364423nm (-274)412nm (+159)A = -333423nm (-294)   412nm (+162)A = -456NNJ!"#$%&'()*3'89:;<=>?
-160!-110
!-60!-10!40!90!140!190!240!290!340!380!400!420!440!Mol CD!Wavelength (nm)
!C5 TPFP 0¡C
!C5 TPFP Room Temp
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!380400-100!-50!0!50!100!150!200!380!400!420!440!Mol CD!Wavelength (nm)
!Room Temperature Hexanes
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HNH2MeHMeH2NHNH2MeNH2H439 (+34)425 (-45)A  = +79439 (-42)425 (+42)A = -84439 (+45)426 (-63)A = -108439 (+55)425 (-75)A = +130NNNNZnNNNNZnNNNNZnNNNNZnLsynLLbaLantiHHHCHNHMeXEt(S)-Amine ComplexPositive ECCDSTl"#$%&'!()*.,
&CG-&M=/)&A-,A8B,=/9&5=/*30&?B&(/&378B5&./=7&),3(73&(/&F11;&8-97&:-,&
<-/-(<=/39#&&X=+/&-:&783&?=9=+/(73&).,23&=9&0=)7(730&?B&783&973,=)&=/73,()4-/&?37G33/&
783&5(,+3&+,-.A&-/&783&(<=/3&(/0&783&378B5&+,-.A&-/&783&A-,A8B,=/#%NNNNPhPhOOOONNNNPhPhPhPhZnZnOOOOZnP2P1nmZn-TPP-Tweezer
host-guest complexZnAZnFavoredNegative ECCDP2P1ZnZnDisfavoredSLP1P2NHNH2OOHLMNHNH2OOHLMNHNH2OOOHHOBrO1.    EDC, DMAP    CH2Cl22.    DIPEA, THFH2NNH2OHNONH2A:B:ZnSTJ"#$%&'!()*/,
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-:&)8=,(5&(<=/39&(/0&(5)-8-59#&&
0,&;3,=2(4M(4-/&-:&Y
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0=(<=/-A,-A(/3&)(,,=3,#&&
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(G(B&:,-<&783&A-,A8B,=/&=/7-&783&53(97&973,=)(55B&)-/+39730&A-9=4-/#&&"/&78=9&
)-/:-,<(4-/E&783&9<(55&(/0&<30=.<&+,-.A9&:()3&783&A-,A8B,=/&(/0&7-&,30.)3&973,=)&
=/73,()4-/9E&783&A-,A8B,=/&95=039&7-G(,0&783&9<(55&+,-.AE&78.9&53(0=/+&7-&(&835=)(5&7G=97&-:&783&
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G=78&783&7G33M3,#&&&>578-.+8&783,3&(,3&,35=(?53&<378-0-5-+=39&(2(=5(?53&:-,&0373,<=/(4-/&-:&)-/@+.,(4-/&

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8=+85B&)-23730#!"#$#e%&C,=A-0(5&X3/9-,9&:-,&><<-/=.<&"-/9&F\-,79&7-&03235-A&(/&F11;&()423&8-97&9B973<&:-,&)8=,(5&+.397&<-53).539&G=78&(&9=/+53&

9=73&-:&([()8<3/7E&G=78-.7&)83<=)(5&03,=2(4M(4-/&-:&783&+.397&<-53).53E&G3,3&=/9A=,30&?B&783&
=<=0(M-53!&&(/0&-L(M-53
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C83&(.78-,9&0=9)5-930&783&9B/7839=9&-:&(/&(<<-/=.<&,3)3A7-,&78(7&3L8=?=730&8=+83,&(n/=7B&:-,&
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&!jN'&G8=)8&
OOOHHOOOHHOOOHHOOOHHNonactinNNNNNNC3-Symmetric Pyrazole Tripod
NONONOC3-Symmetric Oxazoline Tripod
SK$"#$%&'!()*2,
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-L(M-539&(/0&783&78,33&8B0,-+3/9&-:&783&(<<-/=.<&,39.57&=/&783&9353)42=7B&:-,&(<<-/=.<&=-/9&
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)-<A53L&?B&c$K&*)(5q<-5#
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MeMeMePF6LLLL =HNHHHNNNOL =Pyrazole Tripod
Oxazoline Tripod
SKe"#$%&'!()*3,
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R1R1R1ONONONR3R2R3R2R3R2EntryR1R2R3Selectivity(nBuNH3 /tBuNH3 )123MeEtEtPhPhPhPhPhH43040002700SKS"#$%&'!()*4,
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.930&(9&].-,39)3/)3&?(930&93/9-,&:-,&)8=,(5&(<=/39#&&j,3:3,3/4(5&?=/0=/+&:-,&Y
!ZP$PA83/B5378B5(<=/3&-23,&783&Y
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-:&].-,39)3/)3&=/73/9=7B&:-,&783&Y!Z&3/(/4-<3,#SKUONONONHHHPhPhPhAmmonium GuestSelectivityExtraction (%)NH3NH3CO2HH3CNH3CO2H71(R):29(S)8278(S):22(R)6053(S):47(R)41A:B:MSLPhPhPhMLSPhPhPhPhPhPhTripod-(
S)-AmineComplexDisfavoredTripod-(
R)-AmineComplexFavoredSKT"#$%&'!()*5,!
F/(/4-9353)423&,3)-+/=4-/&-:&(<=/39&(&7,=A-0(5&8-97#&&
0,&FL(<A539&-:&
9353)423&?=/0=/+&G=78&)8=,(5&(<=/39#&&C83,3&=9&5=[53&9353)42=7B&G=78&(5(/=/3&<378B5&3973,#&&
1,&1-/:-,<(4-/9&-:&783&0=(973,3-<3,=)&7,=A-0P(<=/3&)-<A53L39#&&Y
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<(*39&?=/0=/+&-:&Y"Z&(<=/3&./:(2-,(?53#!)!"#e%&;39=+/&(/0&XB/7839=9&-:&(&C,=A-0(5&o-97&:-,&F11;&-:&18=,(5&><<-/=.<&"-/9&'(930&-/&783&A,32=-.9&-L(M-5=/3&7,=A-0&9B973<9E&=7&G(9&8BA-7839=M30&78(7&(/&(AA,-A,=(73&
7,=A-0(5&8-97&<-53).53&)-.50&?3&039=+/30&(9&(&,3)3A7-,&(/0&F11;&()423&8-97&<-53).53&:-,&)8=,(5&
(<<-/=.<&9(579#&&C-&<(=/7(=/&783&8=+8&(n/=7B&:-,&(<<-/=.<&=-/9E&783&?3/M3/3&]--,&G-.50&?3&

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()42=7B#&&C83,3:-,3E&:-,&783&=/=4(5&039=+/E&(&?3/M-L(M-53&G(9&)8-93/&(9&783&8373,-)B)53#&&
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.-/&=9&eTU&/<&&
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7,=A-0(5&8-97Z#&"7&=9&=<A3,(423&7-&?3+=/&G=78&(/&()8=,(5&8-97&<-53).53&:-,&F11;#&&C83&8-97&98-.50&:-,<&

(/&()8=,(5&?=/0=/+&A-)*37&9-&78(7&783,3&=9&/-&=/83,3/7&A,3:3,3/)3&:-,&?=/0=/+&3=783,&3/(/4-<3,&
-:&783&(<<-/=.<#&&>D3,&)-<A53L(4-/&G=78&(&)8=,(5&(<<-/=.<&9(57E&783&A-=/7&)8=,(5=7B&-:&783&
(<<-/=.<&G=55&0=)7(73&783&-,=3/7(4-/&-:&783&-L(M-53&(,<9&-:&783&7,=A-0&:-,)=/+&783&7,=A-0&7-&

(0-A7&3=783,&(&)5-)*G=93&Yu&)-<A53LZ&-,&)-./73,)5-)*G=93&835=)=7B&Yv&)-<A53LZ#
"+&&C83,3:-,3E&
783,3&(,3&7G-&0=(973,3-<3,=)&)-<A53L39&A-99=?53&:-,&783&(<<-/=.<P7,=A-0&)-<A53L#&&":&(/&Y
!ZP(<<-/=.<&=9&)-<A53L30&G=78&783&7,=A-0E&78393&0=(973,3-<3,9&(,3&783&Y
!ZPu&)-<A53L&(/0&783&
Y!ZPv&)-<A53L#&&C83&A,3:3,,30&)-<A53L&(/0&783,3:-,3E&835=)=7B&-:&783&7,=A-0&=9&78(7&=/&G8=)8&783&

973,=)&=/73,()4-/9&G=78&783&9.?947.3/79&(7&783&)8=,(5&)3/73,&(,3&<=/=<=M30#&&SKKAr2NONONOPhCH3HAr2Ar3Ar1H3CNH3HPhHAr1CH3HAr2PhCH3Ar3PhCH3HPhHCH3HPhCH3Ar1Ar3Ar2Ar1Ar3B1disfavoredB2favoredB3favoredA1favoredA2disfavoredA3disfavoredB! complexA" complexXXProposed BenzoxazoleTripod
+Benzoxazole Tripod-
(R)-#-methylbenzyl amine Complex(R)-#-methylbenzyl amineNOONONHNHHSKh"#$%&'!()*6,
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)-<A53L&G=78&Y
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1&=9&783&
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=/03A3/03/7&9B973<#&&N-,&3L(<A53E&N=+.,3&!"#J#>$&0373,<=/39&=:&783&973,=)&3/2=,-/<3/7&(?-.7&

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0=9:(2-,30&?3)(.93&783&?3/M-L(M-53&=9&-,=3/730&(G(B&:,-<&783&9<(55&8B0,-+3/E&7-G(,0&783&
5(,+3,&<378B5#&&_23,(55E&783&v&)-<A53L&=9&:(2-,30&G=78&Y
!ZPwP<378B5?3/MB5(<=/3#&&C8=9&)-<A53L&

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783&3/(/4-<3,&Y
"ZPwP<378B5?3/MB5(<=/3E&783&u&)-<A53L&G-.50&?3&:(2-,30#&&C8=9&<3(/9&78(7&
783&3/(/4-<3,9&-:&(&9=/+53&(<<-/=.<&G-.50&=/0.)3&783&-AA-9=73&835=)=7B&=/&783&7,=A-0(5&8-97&

N.,783,<-,3E&(/B&(<<-/=.<&8(2=/+&783&9(<3&(,,(/+3<3/7&-:&9<(55E&<30=.<&(/0&5(,+3&+,-.A9&
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)-/9=03,(4-/9&78(/&783&A-,A8B,=/&7G33M3,&9B973<9&0=9).9930&=/&783&A,32=-.9&)8(A73,9&(9&783,3&
(,3&/-G&78,33&)8,-<-A8-,39&78(7&G=55&=/73,()7&7-&+3/3,(73&783&9=+/(5#&&"/&$JhVE&H(*(/=98=&(/0&

)-PG-,*3,9&03<-/97,(730&78(7&783&)-/@+.,(4-/&-:&)B)5=)&7,=-59&)-.50&?3&0373,<=/30&:,-<&783&
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"!,""&&N-,&783&9.+(,&7,=?3/M-(73E&wP<378B5PyP
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$VZ#""&&C-&./03,97(/0&783&A-9=423&9=+/E&783&)8(=,&:-,<&-:&783&7,=?3/M-(73&G(9&)-/9=03,30#&&C83/&
783&3LA3)730&9=+/&:-,&3()8&A(=,&-:&)8,-<-A8-,39&G(9&0373,<=/30#&&N-,&(55&78,33&A(=,9&YePSE&SPUE&
SKlePUZ&(&A-9=423&9=+/&=9&3LA3)730&(9&783&?3/M-(739&
(,3&-,=3/730&=/&(&)5-)*G=93&:(98=-/#&&g=78&(55&
78,33&A(=,9&3LA3)730&7-&A,-2=03&(&A-9=423&9=+/(5E&(/&-23,(55&A-9=423&9=+/&:-,&783&7,=?3/M-(73&G(9&
3LA3)730&(/0&-?93,230#&&C8=9&A(=,PG=93&(00=42=7B&-:&=/73,()4/+&)8,-<-A8-,39&G(9&(59-&.930&7-&
9.))399:.5&A,30=)7&783&3LA3)730&F11;&9=+/9&:-,&973,-=0(5&7,=?3/M-(739&(/0&9.+(,&737,(?3/M-(739#
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F11;&9=+/(5#&&g83/&783&7,=A-0&=9&=/&783&u&)-<A53LE&783&)8,-<-A8-,39&(,3&-,=3/730&=/&(&
)5-)*G=93&:(98=-/#&&15-)*G=93&835=)=7B&-:&7G-&)8,-<-A8-,39&=9&3LA3)730&7-&+3/3,(73&(&A-9=423&
OOOOOMeOOMeOOOOClOClOClOClOClOCl!-methyl-L-arabinopyranoside2,3,4-tris(p-chlorobenzoate)2342-3 3-42-4OverallPredicted ECCDObserved ECCD246 nm (+81)230 nm (-25)A = +106SKJ"#$%&'!()*+8,
&F11;&-:&(&9.+(,&7,=?3/M-(73#&&C83&-23,(55&F11;&9=+/(5&=9&A,30=)730&?B&
)-/9=03,=/+&783&F11;&9=+/(5&-:&783&78,33&A(=,9&-:&)8,-<-A8-,39#&&F()8&A(=,&=9&A,30=)730&
7-&+3/3,(73&(&A-9=423&F11;&783,3:-,3E&783&7,=?3/M-(73&=9&3LA3)730&7-&A,-2=03&(&A-9=423&
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:(98=-/#&&>55&78,33&A(=,9&G-.50&A,-2=03&(&A-9=423&F11;&78.9E&783&-23,(55&(&A-9=423&F11;&G-.50&
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)-./73,P)5-)*G=93&:(98=-/#&&N-,&3()8&A(=,&-:&=/73,()4/+&)8,-<-A8-,39E&(&)-./73,P)5-)*G=93&

835=)=7B&(/0&/3+(423&9=+/&(,3&3LA3)730#&&>&/3+(423&F11;&9=+/(5&=9&A,30=)730&:-,&783&v&)-<A53L#&&&C83&A(=,PG=93&(00=42=7B&-:&)8,-<-A8-,39&)(/&?3&(AA5=30&7-&783&A,-A-930&7,=A-0(5&8-97&
7-&A,30=)7&783&9=+/&-:&783&F11;&9=+/(5&?(930&-/&783&A,3:3,,30&835=)=7B&-:&783&8-97P+.397&)-<A53L&&

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A,32=-.95BE&783&v&)-<A53L&=9&:(2-,30&:-,&Y
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)-<A53L&(/0&(&A-9=423&F11;&9=+/(5&G-.50&?3&3LA3)730&:-,&Y
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7,=A-0&G(9&039=+/30&9.)8&78(7&783&?3/M-L(M-53&)8,-<-A8-,39&G-.50&?3&?.=57&78,-.+8&(/&()=0&

)(7(5BM30&)B)5=M(4-/&-:&
'P(<=/-A83/-5&G=78&$ESETP7,=9PY()34)&()=0ZPeEUEKP7,=<378B5?3/M3/3&=/&
783&@/(5&973A&(/0&783&7,=9()=0&G-.50&?3&9B/7839=M30&:,-<&783&)-<<3,)=(55B&(2(=5(?53&<39=7B53/3&

YX)83<3&!"#$&>Z#&&ShVNONONONH3X!! complex" complexIf (S)-amineIf (R)-amineSMLAr2Ar3Ar1Ar1Ar3Ar2!#+-Positive ECCD$ (nm)!#+-Negative ECCD$ (nm)Ar2Ar3Ar1SMLAr1Ar3Ar2SMLSh$"#$%&'!()*++,
&j,-A-930&</3<-/=)&:-,&F11;&-:&)8=,(5&(<<-/=.<&9(579&G=78&783&
?3/M-L(M-53&7,=A-0#&&>/&Y
"Z&(<=/3&=9&3LA3)730&7-&?=/0&:(2-,(?5B&G=78&783&7,=A-0&=/&783&
u&)-<A53L#&&C83&u&)-<A53L&=9&3LA3)730&7-&A,-2=03&(&A-9=423&F11;&).,23&?(930&-/&A(=,P
G=93&(00=42=7B&-:&)8,-<-A8-,39#&&C83,3:-,3E&(/&
Y"Z&(<=/3&=9&3LA3)730&7-&+3/3,(73&(&
A-9=423&F11;#&&C83&Y
!Z&(<=/3&=9&3LA3)730&7-&+=23&(&/3+(423&F11;#&XB/7839=9&-:&783&7,=A-0&?3+(/&G=78&783&=/97(55(4-/&-:&78,33&?,-<-<378B53/3&./=79&
78,-.+8&N,=3035P1,(D9&G=78&A(,(:-,<(5038B3&=/&783&A,393/)3&-:&o',&YX)83<3&!"#$&'Z#
"#&&C83&
BrBrBrHBr (33% in HOAc)AcOHreflux, 24 h76%(CH2O)n(3.3 equiv)NaCN (4.5 equiv)acetone, H2Oreflux, 12 h85%NCCNCNNaOH 3 MH2O2 (30%)reflux, 24 hquantitativeHO2CCO2HCO2HVI.2VI.3VI.4HOOOOHOOHNONONOOHNH210 equivPPA, 
150 ¡C, 12 h30%VI.1!A:B:!NONONOVI.1OHNH2She9:;'<'!()*+,
&XB/7839=9&-:&783&?3/M-L(M-53&7,=A-0#&&
0,&I37,-9B/7839=9&:,-<&<39=7B53/3#&
1,&N-,G(,0&9B/7839=9&A,-2=0=/+&783&7,=A-0#?,-<=039&G3,3&783/&,3A5()30&?B&)B(/-&+,-.A9&?B&9.?947.4-/&G=78&H(1H#
"&&&X(A-/=@)(4-/&-:&
783&)B(/-&+,-.A9&G=78&H(_o&(/0&o
"_""%&A,-2=030&783&()=0&=/&KTz&B=350&:-,&783&78,33&973A9#&&
C8=9&9B/7839=9&-:&783&7,=9()=0&8(9&?33/&9)(530&7-&T&+&G=78-.7&(\3)4/+&783&-23,(55&B=350#&&g=78&783&
()=0&=/&8(/0E&783&7,=A-0&G(9&9B/7839=M30&?B&(&A-5BA8-9A8-,=)&()=0&Yjj>Z&)(7(5BM30&)B)5=M(4-/&
G=78&-P(<=/-A83/-5#
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7-&8(23&(&t
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!10-5 M!2x10-5 M!3x10-5 M!4x10-5 M!5x10-5 M!ShS"#$%&'!()*+-,
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t&p&eh$&/<{&p&eVETVV
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":&783&)-<A53L&:-,<30E&783,3&98-.50&?3&)83<=)(5&98=D&)8(/+39&-:&783&(<<-/=.<&0.3&7-&
98=350=/+&-,&0398=350=/+&=/73,()4-/9&G=78&783&(,-<(4)&?3/-L(M-53&)8,-<-A8-,39#&&
&"/=4(55BE&)-<A53L(4-/&G=78&783&83L(].-,-A8-9A8(73&(<<-/=.<&9(57&-:&wP
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)-PG-,*3,9#&&N=,97E&783&8B0,-)85-,=)&()=0&9(57&-:&783&(<=/3&G(9&+3/3,(730&?B&(00=4-/&-:&

8B0,-)85-,=)&()=0&7-&783&(<=/3&=/&1o
"15"#&&C83&o15&9(57&G(9&=9-5(730&?B&,3<-2(5&-:&1o
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##&&C8=9&G(9&783/&)3/7,=:.+30&:-,&
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ShUNH21. conc. HCl    CH2Cl22. NaPF6 (excess)    D2ONH3¥PF6VI.5H3CNONONONH3H3CHfgcHHHHHHabccdeNOONHNHHPF6PF6HHHHHProtonAmine(ppm)Tripod
(ppm)Complex(ppm)abcdefgNANA7.30 - 7.24 (m)7.16 (m)NA4.04 (q)J = 6.5HzNA1.31 (d)J = 6.5 Hz7.63 (m)7.42 (m)7.25 (m)4.39 (s)NA2.52 (s)NA7.57 (m)7.42 (m)7.32 - 7.26 (m)7.26 - 7.19 (m)3.40 (s)4.07 (q)J = 6.5 Hz2.50 (s)1.37 (d)J = 6.5 HzONA:B:ShT"#$%&'!()*+.,!
1-<A53L(4-/&-:&
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783&?3/M-L(M-53&7,=A-0#&&
0,!
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##&&>55&-:&783&(<=/3&
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"15"#&&g=78&78=9&A,-)30.,3E&783&
737,(].-,-?-,(73&9(57&-:&Y"ZPSP<378B5PeP?.7(<=/3&G(9&=9-5(730&783/&9.?Q3)730&7-&H6I&97.0B#&&
&C83&H6I&97.0B&G(9&@,97&)-/0.)730&=/&1;15
##&&kA-/&(00=4-/&-:&7G-&3R.=2(53/79&-:&783&
(<=/3&7-&783&7,=A-0E&783,3&G(9&/-&9=+/=@)(/7&)8(/+3&=/&783&)83<=)(5&98=D9&-:&3=783,&783&7,=A-0&

-,&783&(<<-/=.<#&&"7&G(9&-?93,230&78(7&783&(<<-/=.<&G-.50&?3+=/&7-&A,3)=A=7(73&=/&1;15
##&&
X-E&<=L30&9-523/7&9B973<9&G3,3&32(5.(730&7-&3/9.,3&9-5.?=5=7B&-:&783&(<=/3#&&'-78&1;15
#q0'P()37-/3&(/0&1;15
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)-<A53L&:-,<(4-/&G(9&-?93,230#&&
&N-,&1;15
#q1;#_;E&G83/&$&3R.=2(53/7&-:&783&(<=/3&G(9&(0030E&5=[53&)8(/+3&G(9&
-?93,230&:-,&783&(<=/3&A,-7-/9&YN=+.,3&!"#$U&'Z#&&o-G323,E&95=+87&98=D9&-:&783&7,=A-0&A,-7-/9&

.A@350&G(9&-?93,230#&&g=78&783&(00=4-/&-:&e&3R.=2(53/79&-:&783&(<=/3E&783&7,=A-0&9=+/(59&
.A@350&98=D&?B&(AA,-L=<(735B&V#T&AA<E&(5-/+&G=78&9<(55&.A@350&98=D9&:-,&(55&783&(<=/3&A,-7-/9&

YcV#VT&AA<Z#&&C83&.A@350&98=D&-:&783&(<=/3&A,-7-/9&=/0=)(739&78(7&783B&(,3&?3=/+&98=35030#&&C8=9&
=9&3LA3)730&(9&783&(<=/3&=9&9=7.(730&=/&783&98=350=/+&)-/3&-:&783&?3/M3/3&]--,&(/0&A-99=?5B&783&
98=350=/+&)-/3&-:&783&?3/M-L(M-53#ShKHBF4 (aq)MeOHNH3¥BF4NH2H3CNONONOH3CCH3NH3CH3HHfghiHHHHHHabccdeBF4VI.6ProtonAmine(ppm)Tripod
(ppm)abcdefgNANANANA2.93 (quin)J = 7.0 HzNA1.72 (sextet)J = 7.0 Hz7.57 (m)7.37 (m)7.21 (m)4.35 (s)NA2.47 (s)NAA:B:1 equiv AmineComplex(ppm)2 equiv AmineComplex(ppm)7.54 (m)7.34 (m)7.19 (m)4.32 (s)2.92 (quin)J = 6.5 Hz2.44 (s)1.72 (sextet)J = 6.5 Hz7.49 (m)7.30 (m)7.15 (m)4.29 (s)2.88 (q)J = 6.5 Hz2.40 (s)1.68 (sextet)J = 6.5 Hzhi1.12 (d)J = 6.5 Hz0.88 (dd)J = 13.5, 7.0 HzNANA1.11 
(d)J = 6.5 Hz0.88 (dd)J = 13.0, 7.0 Hz1.08 (d)J = 6.5 Hz0.84 (dd)J = 13.5, 7.0 HzShh"#$%&'!()*+/,
&H6I&97.0B&-:&783&?3/M-L(M-53&7,=A-0&G=78&
Y"ZPSP<378B5PeP?.7(<=/3&737,(].-,-?-,(73&=/&1;15
#q1;#_;#&&
0,!
XB/7839=9&-:&783&(<<-/=.<&9(57#&&
1,&C(?53&-:&
H6I&0(7(#&&$&3R.=2(53/7&98-G30&5=[53&)8(/+3&8-G323,E&G=78&e&3R.=2(53/79&(55&-:&783&
7,=A-0&(/0&(<=/3&9=+/(59&98=D&.A@350&=/0=)(4/+&A-99=?53&)-<A53L&:-,<(4-/#&H>&p&/-7&
(AA5=)(?53&"/&1;15
#q0'P()37-/3E&(7&$&(/0&S&3R.=2(53/79&-:&(<=/3&=/&(&9-5.4-/&-:&783&7,=A-0E&783,3&
G3,3&7G-&9379&-:&A3(*9&)-,,39A-/0=/+&7-&783&(<=/3&YN=+.,3&!"#$TZ#&&_/3&937&)-,,35(730&G355&G=78&
783&9=+/(59&:-,&783&(<<-/=.<&9(57#&&C83&93)-/0&937&-:&A3(*9&G3,3&98=D30&,35(423&7-&783&
(<<-/=.<#&&C83&(<=/3&<378=/3&A,-7-/&98-G30&783&5(,+397&)8(/+3&?3=/+&0-G/@350&98=D30&?B&

V#U&AA<#&&C83&<378B5&0-.?537&G(9&(59-&0-G/@350&98=D30&?.7&7-&(&53993,&3L73/7#&&C83&=9-A,-AB5&
<378=/3&(/0&<378B5&A,-7-/9&98-G30&(&95=+87&.A@350&98=D#&&>7&:-.,&3R.=2(53/79&-:&(<=/3E&783&
(<=/3&)83<=)(5&98=D9&<(7)8&783&)83<=)(5&98=D9&-:&783&(<<-/=.<&G8=)8&G-.50&=/0=)(73&78(7&

783&)-<A53L&8(9&0=9=/73+,(730#&&g=78&-/3&3R.=2(53/7&-:&783&(<<-/=.<E&783&=/73+,(4-/9&-:&783&
(<=/3&<378=/3&A3(*9&98-G9&78(7&8(5:&-:&783&(<<-/=.<&=9&=/73,()4/+&G=78&783&7,=A-0&(/0&8(5:&=9&
/-7#&&C83&9(<3&=9&-?93,230&G=78&S&3R.=2(53/79&-:&783&(<<-/=.<#&&C8=9&=9&=/73,394/+&(9&(+(=/&=7&

)-.50&9.++397&78(7&(578-.+8&783&(<=/3&=/73,()79&G=78&783&7,=A-0&=7&=9&/-7&=/&783&$%$&)-<A53L&78(7&
=9&039=,30#&&>59-E&(&0-G/@350&98=D&-:&783&(<<-/=.<&<378=/3&=9&)-/)3,/=/+#&&"7&=9&A,30=)730&78(7&
=/&(&$%$&)-<A53LE&78=9&<378=/3&98-.50&?3&9=7.(730&=/&783&98=350=/+&)-/3&-:&783&?3/M3/3&)-,3#&&

C83,3:-,3E&783,3&=9&32=03/)3&-:&=/73,()4-/&G=78&783&7,=A-0&8-G323,E&5=*35B&/-7&=/&(&$%$&)-<A53L#&&
&F/)-.,(+30&78(7&783,3&G(9&9-<3&7BA3&-:&)-<A53L&:-,<(4-/&?37G33/&783&?3/M-L(M-53&
7,=A-0&(/0&783&(<<-/=.<&9(57E&(&93(,)8&7-&@/0&783&-A4<(5&)-/0=4-/9&:-,&F11;&(/(5B9=9&-:&783&

)-<A53L&G(9&./03,7(*3/#&&k/:-,7./(735BE&(D3,&)8(/+=/+&-:&9-523/7&Y1o15
#E&1o
#_oE&83L(/39ZE&
)-/)3/7,(4-/&Y$V
$%&6&7-&$V
$&&6Z&(/0&73<A3,(7.,3&YP$V&
01E&V&
01E&,7ZE&F11;&G(9&/-7&-?93,230&
G=78&78=9&9B973<#&&o-G323,E&G=78&H6I&32=03/)3&9.++394/+&)-<A53L&:-,<(4-/E&-A4<=M(4-/&-:&
783&7,=A-0&98-.50&?3&./03,7(*3/&=/&783&:.7.,3#ShlH3CNONONOH3CCH3NH3CH3HHfghiHHHHHHabccdeBF4ProtonAmine(ppm)Tripod
(ppm)1 equiv AmineComplex(ppm)abcdefgNANANANA3.19 (quin)J = 6.5HzNA1.88 (sextet)J = 6.5 Hz7.54 (m)7.33 (m)7.16 (m)4.31 (s)NA2.44 (s)NA7.50 (m)7.30 (m)7.17 (m)4.27 (s)3.66 (quin) J = 6.5 Hz3.17 (quin) J = 6.5 Hz2.40 (s)1.89 (m)3 equiv AmineComplex(ppm)4 equiv AmineComplex(ppm)7.41 (m)7.22 (m)7.05 (m)4.20 (s)3.12 (quin)J = 6.0 Hz2.32 (s)1.80 (sextet)J = 6.5 Hzhi1.22 (d)J = 6.5 Hz0.91 (dd)J = 16.0, 7.0 HzNANA1.26 (d) J  = 7.0 Hz1.22 (d) J  = 7.0 Hz0.90 (dd) J = 14.0, 7.0 Hz0.86 (dd) J = 17.0, 7.0 Hz1.15 (d)J = 6.5 Hz0.82 (dd)J = 15.5, 7.0 Hz7.38 (m)7.20 (m)7.02 (m)4.18 (s)3.48 (quin) J = 6.5 Hz3.04 (quin) J = 6.0 Hz2.30 (s)1.77 (sextet) J = 7.0 Hz1.72 (sextet) J = 6.5 Hz1.10 (d) J = 6.5 Hz1.08 (d) J = 6.5 Hz0.79 (dd) J = 10.0, 7.0 Hz0.73 (dd) J = 21.0, 6.5 HzShJ"#$%&'!()*+2,
&H6I&97.0B&-:&783&?3/M-L(M-53&7,=A-0&G=78&
Y"ZPSP<378B5PeP?.7(<=/3&737,(].-,-?-,(73&=/&1;15#q0'P()37-/3#&&H>&p&/-7&(AA5=)(?53
!"#U%&1-/)5.9=-/9&(/0&X.++394-/9&:-,&N.7.,3&X7.0=39&C83,3&(,3&9323,(5&G(B9&=/&G8=)8&783&7,=A-0&)-.50&?3&:.,783,&-A4<=M30&7-&(/&F11;&()423&
8-97&<-53).53#&&_/3&<(Q-,&5=<=7(4-/&-:&783&?3/M-L(M-53&7,=A-0&=9&783&t
.-/&-:&783&)8,-<-A8-,3#&&
C83&(?9-,?(/)3&-:&?3/M-L(M-53&=9&)5-93&7-&783&(?9-,?(/)3&-:&)8,-<-A8-,39&)-<<-/5B&

3/)-./73,30&=/&-,+(/=)&)-<A-./09#&&C83&3LA3)730&F11;&:-,&?3/MB5(<=/3&G=78&783&?3/M-L(M-53&
7,=A-0&G-.50&?3&)-<A5=)(730&?B&)-.A5=/+&-:&783&?3/M-L(M-53&)8,-<-A8-,39&G=78&783&?3/M3/3&

-:&783&(<=/3#&&>&7,=A-0&G=78&(&,30&98=D30&)8,-<-A8-,3&G-.50&A,323/7&)-.A5=/+&G=78&783&+.397&
9.?97,(73#&&C-&78=9&3/0E&3L73/0=/+&783&)-/Q.+(4-/&-:&783&)8,-<-A8-,3&G-.50&,30&98=D&783&
(?9-,?(/)3#&&H(A878-L(M-539&Yt
.-/&|&SVV&/<ZE
"*&(/78,-L(M-53E&A83/(/78,-L(M-53&Yt
.-/&|&SSV&/<Z
#+&98-.50&?3&)-/9=03,30#&&
&6-0=@)(4-/&-:&783&8373,-)B)5=)&A-,4-/&-:&783&)8,-<-A8-,3&)-.50&?3&(/-783,&,-.73&-:&
-A4<=M(4-/#&&>9&98-G/E&=<=0(M-53&?(930&)8,-<-A8-,39&98-.50&:-,<&97,-/+3,&8B0,-+3/&?-/09&
G=78&783&(<<-/=.<&78(/&-L(M-53&0.3&7-&783&=/),3(930&?(9=)=7B&-:&783&8373,-)B)53#
!(&&>00=4-/(55BE&78=-L(M-53&)-/7(=/=/+&)8,-<-A8-,39&)-.50&(59-&?3&)-/9=03,30&(9&783&?(9=)=7B&-:&
78=-L(M-53&Ye#TZ&5=39&?37G33/&78(7&-:&783&-L(M-53&YV#lE&53(97&?(9=)Z&(/0&=<=0(M-53&YU#JE&<-97&
?(9=)Z#&&
&N=/(55BE&(9&0=9).9930&(?-23E&>8/&(/0&)-PG-,*3,9&-?93,230&3/8(/)30&?=/0=/+&(n/=439&
:-,&(5*B5(<<-/=.<9&G83/&7,=378B5?3/M3/3&G(9&.930&:-,&783&]--,&-:&783&7,=A-0#
!'&&C83B&
8BA-7839=M30&78(7&783&4+873,&?=/0=/+&G(9&0.3&7-&A,3P-,+(/=M(4-/&-:&783&?=/0=/+&A-)*37#&&

C83,3:-,3E&7,=A-09&G=78&783&7,=378B5?3/M3/3&)-,3&98-.50&?3&)-/9=03,30#&&":&A,3P-,+(/=M(4-/&-:&
783&A-)*37&8(9&?33/&98-G/&7-&3/8(/)3&?=/0=/+&(n/=439E&783/&=7&<(B&(59-&A,-<-73&:-,<(4-/&
SlV-:&783&$%$&7,=A-0P(<<-/=.<&)-<A53L#&&6,#&}./&i8(/+&8(9&(5,3(0B&?3+./&G-,*&-/&7,=A-09&G=78&
7,=378B5?3/M3/3&]--,#Sl$!"#T%&FLA3,=<3/7(5&j,-)30.,39!"#T#$%&W3/3,(5&j,-)30.,39&g83,3&=7&=9&97(730&78(7&0,B&1o
"15"&-,&0,B&7-5.3/3&G(9&.930E&783&9-523/7&G(9&0=945530&-23,&
1(o"#&&;,B&CoN&(/0&0=378B5&3783,&G3,3&-?7(=/30&?B&0=9455(4-/&:,-<&9-0=.<&?3/M-A83/-/3&
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