The Strecker synthesis is a multicomponent route to α-amino acids through formation and subsequent hydrolysis of an α-aminonitrile. An aldehyde or ketone first condenses with ammonia or an amine to form an imine or iminium species; cyanide then adds to the imine carbon, generating an α-aminonitrile whose nitrile group is hydrolyzed to a carboxylic acid [1]. The carbonyl carbon becomes the α-carbon of the amino-acid product, while the nitrogen and cyanide supply the amino and carboxyl-derived functionalities, respectively. When a prochiral imine is attacked in an achiral environment, a racemic product normally results. Catalytic asymmetric Strecker variants use chiral catalysts to discriminate the two imine faces and furnish enantioenriched α-aminonitriles [2]. The reaction is distinguished from direct reductive amination because cyanide forms a new carbon–carbon bond and the nitrile, rather than a reducing agent, is the immediate precursor of the carboxyl group.
Organic Chemistry Synthesis Methods • Organic Chemistry • Chemistry • Physical Sciences