Diastereoselection in the conjugate additions of organocopper reagents to N-enoyloxazolidinones

Abstract

A survey of conjugate additions of Yamamoto organocopper reagents to N- enoyl-4-substituted oxazolidinones is reported. Diastereofacial selectivity is reversed for 4-phenyl and 4-benzyloxazolidinones of the same relative configuration. Alkenylcopper reagents demonstrate superior results in asymmetric additions using the 4-phenyloxazolidinone auxiliary.