Asymmetric hydrocyanation of hydrazones catalyzed by in situ formed O-silylated BINOL-phosphate: a convenient access to versatile alpha-hydrazino acids.

A first organocatalytic enantioselective route was developed for the conversion of readily prepared and air stable aliphatic hydrazones to synthetically valuable alpha-hydrazinonitriles. This BINOL-phosphate catalyzed Strecker-type reaction (see scheme, Ar = p-NO(2)-Ph) provides a new practical and direct route to alpha-hydrazino acids of synthetic and biological importance. The actually active catalyst is proposed to be an in situ formed O-silylated BINOL-phosphate, thus shifting the nature of catalysis from Brønsted acid to Lewis acid organocatalysis.