Approaches to catalytic asymmetric formation and reactions of lithium enolates

Abstract

Studies have been made to explore the use of chiral chelated lithium amides or their corresponding amines for enantioselective reactions. Some of our results are discussed in terms of enantioselective deprotonation of prochiral cyclic ketones, kinetic resolution of racemic 2-substituted cyclohexanones, regioselective deprotonation of optically active 3-keto steroids, enantioselective alkylation and protonation of achiral lithium enolates. Examples of catalytic asymmetric deprotonation and alkylation by the present strategy are also discussed. © 1995, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.