ENANTIOSELECTIVE REACTIONS USING CHIRAL LITHIUM AMIDES

Lithium dialkylamides such as lithium diisopropylamide (LDA) are now used widely as bases of choice in synthetic organic chemistry. This article describes a relatively new area of asymmetric synthesis in which chiral lithium amide bases act both as bases and as chiral auxiliaries in the reactions to give optically active products enantioselectively. Examples of enantioselective deprotonation, enantioselective protonation, enantioselective carbon-carbon bond formation, and enantioselective dehydrohalogenation are reviewed. Since generation of carbanions by bases and their reactions constitute the backbone of organic synthesis, the chemistry presented here offers attractive opportunities for further developments. © 1990, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.