Stereochemistry of the Asymmetric Oxidation of Ketone Enolates Using (Camphorylsulfonyl)oxaziridines

Abstract

Asymmetric oxidation of the sodium enolates of ketones using chiral oxaziridines (+)-(2R,8aS)-l and (-)-(2S,8aR)-2 affords a-hydroxy ketones 4 in high optical purity (69-95% ee). An open transition state, controlled by nonbonded steric interactions, is proposed as being responsible for the chiral recognition. © 1986, American Chemical Society. All rights reserved.