Relative Stereoselectivity of the Reactions of (2R,3R)-Dibenzoyloxysuccinic and (2R,3S)-2,3-Dibenzoyloxysuccinic Anhydrides With Chiral Amines and Alcohols

Abstract

Stereoselectivities of the reactions of (2R,3R)- and (2R,3S)-2,3-dibenzoyloxysuccinic anhydrides with some chiral arnines and alcohols have been determined by ¹H n.m.r. analysis of the mixture of diastereomers. In all cases the stereoselectivity was higher for the (2R,3R)-isomer and a simple model has been proposed to explain this. The structure of one of the diastereomers from the (2R,3S)-isomer has been confirmed by synthesis.