Stereochemical Studies. L. Reductive Decyanization of α-Amino Nitriles with Sodium in Liquid Ammonia. An Alternate Method for the Application to the Asymmetric Synthesis of optically Active Natural Products

Abstract

An alternate method for reductive decyanization of α-amino nitriles to the corresponding amines was exploited using sodium in liquid ammonia. This method eliminated the limitation encountered in the reaction with sodium borohydride. Using this new process, optically active α-amino nitrile (8) was decyanized to 9 without racemization.