Novel catalysts for the enantioselective Henry reaction

Abstract

Two novel catalytic systems based on the CuII complexes with N-(3,5-dibromo-2-hydroxybenzyl)- and N-(2-hydroxy-3-nitrobenzyl)-(S)-α,α-diphenylprolinols were developed. These systems catalyze the condensation of 4-nitrobenzaldehyde with nitromethane to produce S-nitroaldol with maximum enantiomeric excess of >90% (99% yield). The reactions of nitromethane with aliphatic aldehydes give the corresponding products in the yields above 80% and ee > 90%.