A large family of chiral boroxinate catalysts derived from the VANOL and VAPOL ligands were synthesized using various protocols developed here within. In order to study these chiral Brønsted acids, a modified procedure for the Wulff catalytic asymmetric aziridination reaction was developed, which is referred to as the 6-component AZ reaction throughout this dissertation. Electronics and sterics were both studied in the B3 catalyst system via altering the phenol or alcohol derivative incorporated into the boroxinate ring of the B3 catalyst. It was realized that electron rich phenols and alcohols allowed for higher enantioselectivities to be obtained in the AZ reactions whereas electron deficient phenols decreased the enantioselectivities observed in the AZ reaction. Both proton and boron NMR studies were performed on the B3 catalyst system to better understand the non-covalent interactions between the imine and B3 catalyst. A multi-component AZ reaction was developed, which eliminated the need for synthesizing the imine precursors for the AZ reaction. Using a one-pot protocol can be highly beneficial when synthesizing aliphatic aziridines due to side reactions occurring when attempting to synthesize and isolate the imine precursors. It was found with this specific protocol that benzoic acid was an important additive, which promoted full conversion of imines to aziridines. Since the VANOL and VAPOL ligands are based on the linear BINOL ligand, a series of reactions were performed in order to generate various BINOL borate species. Attempts were made to synthesize B1, B2, and BLA BINOL species. Unfortunately, B1 proved to be very difficult to generate and was not produced here in any substantial amount. However, Kaufmann's propeller, B2 and BLA species were generated using various protocols.
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