A Facile One-Pot Conversion of Acetates of the Baylis−Hillman Adducts to [E]-α-Methylcinnamic Acids

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.