Synthesis of (R)-3,4-Diaminobutanoic Acid by Desymmetrization of Dimethyl 3-(Benzylamino)glutarate through Enzymatic Ammonolysis

Abstract

Lipase B from Candida antarctica is shown to be a highly efficient catalyst for the desymmetrization of dimethyl 3-(benzylamino)glutarate (1) through aminolysis and ammonolysis reactions. Using this procedure, enantiopure monoamides are obtained in high yield. The synthetic value of these compounds is demonstrated by the preparation of an enantiopure nonnatural amino acid, i.e. (R)-3,4-diaminobutanoic acid [(+)-12].