Desymmetrization of prochiral anhydrides with Evans’ oxazolidinones: an efficient route to homochiral glutaric and adipic acid derivatives

Abstract

The prochiral recognition between enantiotopic carbonyl groups in the reaction of 3-substituted glutaric and 3,4-disubstituted adipic anhydrides with anions of Evans’ oxazolidinones has been investigated. Each of the σ-symmetric anhydrides provided a diastereoisomeric mixture of half-acids which were separated either by fractional crystallization or by column chromatography of their esters. The diastereoselectivity of the desymmetrization reaction is dependent on the substituents present in the anhydrides.