One-pot synthesis of allyl thioacetate from benzaldehydes and activated alkenes using the Morita-Baylis-Hillman reaction as a key step

Abstract

An efficient, regioselective and steresoselecitive one-pot protocol for the synthesis of (Z)-S-2-alkoxycarbonyl-3-acylallyl ethanethioates and (E)-S-2-cyano-3-acylallyl ethanethioates from benzaldehydes and activated alkenes (methyl acrylate and acrylonitrile) was developed. Our method consisted of Morita-Baylis-Hillman reaction of benzaldehydes and activated alkenes using DABCO followed by acetylation using acetic anhydride and a catalytic amount of DMAP, and S(N)2 ' reaction with potassium thioacetate in DMF. The first two reactions proceeded under solvent-free condition.