Catalytic asymmetric acylation of (silyloxy)nitrile anions

Abstract

An enantiopure (salen)aluminum alkoxide complex catalyzes the asymmetric coupling of acylsilanes and cyanoformate esters [Eq. (1), R = Bn, Et]. The reactions afford unsymmetrical, fully protected malonic acid derivatives that may be elaborated to nonnatural β-amino acid derivatives, and represent the first asymmetric catalytic reactions involving protected cyanohydrin anions.