Some recent applications of alpha-amino nitrile chemistry

Bifunctional alpha-amino nitriles are not only versatile intermediates in o rganic synthesis but also exhibit a valuable dual reactivity, which has bee n utilized in a broad range of synthetic applications. This review highligh ts recent developments in the chemistry of alpha-amino nitriles, including asymmetric synthesis of alpha-amino acids via Strecker reactions using chir al auxiliaries and catalysts, alpha-amino nitriles as masked iminium ion eq uivalents in cationic reactions and the synthesis of natural products and h eterocycles, and alpha-metallation to provide nucleophilic acyl anion equiv alents and applications to asymmetric Umpolung reactions.