Asymmetric conjugate additions of TMSI promoted monoorganocuprate reagents, Li[RCuI], to various N-enoyl oxazolidinones

Diastereoselective conjugate additions to different alpha,beta-unsaturated N-acyl oxazolidinones using various monoorganocuprate reagents, Li[RCuI], are described. The TMSI activated conjugate addition reactions provided high yields (80-98%) and reversed major diastereomers (70 96% de) compared to the conventional copper(I)-promoted additions of Grignard reagents or the addition of Li[RCuI] to precomplexed MgBr2/imides. (C) 2002 Elsevier Science Ltd. All rights reserved.