A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids

Abstract

A simple and convenient stereoselective synthesis of [E]-α- methylcinnamic acids via the nucleophilic addition of hydride ion from sodium borohydride to methyl 3-acetoxy-3-aryl-2-methylenepropanoates followed by hydrolysis and crystallization is described. Efficacy of this methodology in the synthesis of [E]-p-(myristyloxy)-α-methylcinnamic acid, an active hypolipidemic agent, and [E]-p-(carbomethoxy)-α-methylcinnamic acid, a valuable synthon for an orally active serine protease inhibitor, is also demonstrated.