Asymmetric Oxidation of Chiral Enolates in the Preparation of Acyclic Tertiary α-Hydroxy Amides in High Optical Purity

Abstract

Asymmetric oxidation of chiral acyclic, tetrasubstituted enolate 4c with oxaziridines (+)-1/(̶)-2 in the presence and absence of HMPA affords optically active tertiary α-hydroxy amide 5c in high optical purity (88-91% de). The application of (+)-1/(̶)-2 as “chiral probes” of enolate-electrophile reaction mechanisms is proposed. © 1987, American Chemical Society. All rights reserved.