Some recent applications of α-amino nitrile chemistry

Bifunctional alpha-amino nitriles are not only versatile intermediates in organic synthesis but also exhibit a valuable dual reactivity, which has been utilized in a broad range of synthetic applications. This review highlights recent developments in the chemistry of alpha-amino nitriles, including asymmetric synthesis of alpha-amino acids via Strecker reactions using chiral auxiliaries and catalysts, alpha-amino nitriles as masked iminium ion equivalents in cationic reactions and the synthesis of natural products and heterocycles, and alpha-metallation to provide nucleophilic acyl anion equivalents and applications to asymmetric Umpolung reactions.