A convenient synthesis of racemic and optically active 1-aza-1,3-dienes derived from gamma-amino esters: reduction to alpha,beta-unsaturated and saturated gamma-amino acid derivatives

A simple synthesis of racemic and optically active 1-azadienes derived from gamma -amino eaters by olefination reaction of alkyl glyoxylates and funct ionalized phosphonium salts or phosphine oxides is reported. Selective redu ction of these 1-azadienes with hydrides yields (E)-gamma -amino-alpha,beta -unsaturated esters. A simple procedure for the preparation of saturated g amma -amino acids and gamma -amino esters from the previously synthesized v inylogous amino esters is also described. (C) 2001 Elsevier Science Ltd. Al l rights reserved.