An enantio selective nucleophilic addition of α, β-unsaturated trifluoromethylketones catalyzed by L-proline derivatives

An unexpected enantioselective 1,2-aldol reaction of acetone with alpha, beta-unsaturated trifluoromethylketone catalyzed by L-proline derivative was described. The absolute configuration of the resulting chiral product was assigned based on a single crystal X-ray diffraction analysis. Structure-reactivity study of this organocatalytic system was briefly discussed. A reaction mechanism was tentatively postulated. (C) 2007 Elsevier Ltd. All rights reserved.