There are four chapters in this dissertation. In Chapter I, a brief review oforganocatalytic Morita-Baylis-Hillman (MBH) reaction is discussed, which covers themechanisms of N-based and P-based catalytic cycles, the asymmetric format of MBHreaction with different catalyst systems, the application of the MBH reaction and itsproducts, and the deviation of the MBH reaction—the Lewis base catalyzed cyclizationreactions. Based on the modified MBH reaction—the formal [4+2] cycloaddition reaction,in Chapter II, we demonstrate a fast assembly towards the synthesis of substitutedhexahydro-2H-chromenes in high stereoselectivity, containing up to 5 contiguousstereocenters via consecutive [4+2]/[4+2] cycloaddition reactions. Inspired by twoobservations from the reactions in Chapter II, methods of a consecutive [4+2]cycloaddition/Brønsted acid catalyzed rearrangement and a consecutive [4+2]cycloaddition/base catalyzed rearrangement toward the synthesis of chiral cyclohex-2-ones and chiral 4H-pyrans, respectively, have been reported in Chapter III. Gaining theinspiration from both Chapter II and Chapter III, in Chapter IV, we describe amidinemediated the synthesis of pyran derivatives through formal [1,5]-H shift. Furthermore, arearrangement of some of these pyrans to furnish phenolic derivatives under acidicconditions is also report. Lastly, incorporation of primary amines in the synthesis ofcarbocyclic beta-amino ester from dihydropyran has been investigated as well
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