The role of reversibility in the enantioselective conjugate addition of α,α-disubstituted aldehydes to nitro-olefins catalyzed by primary amine thioureas

Abstract

Kinetic and spectroscopic studies probing the conjugate addition of 2-phenylpropanal to nitro-olefins catalyzed by two different primary amine thiourea catalysts reveal the nature of the catalyst resting state and demonstrate that reversibility of the reaction is implicated in cases of low enantio- and diastereoselectivity.