Stereoselective Synthesis of α,β-Diamino Nitriles from Amino Acids

Abstract

α-Amino acids 1 are readily converted into the corresponding N, N-dibenzylamino aldehydes 2 which in turn serve as starting materials for enantiomerically pure α- N,N-dibenzylamino aldimines 5, 6 and 7 having benzyl, tosyl and trimethylsilyl groups, respectively, at the aldimine nitrogen atom. All three classes of chiral aldimines undergo stereoselective Lewis acid promoted Me3SiCN addition reactions with non-chelation controlled formation of the corresponding α,β-diamino nitriles. All of the reaction sequences occur without any racemization.