Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols

Simple prolinamides 1a-f were synthesized, and their catalytic effects on the direct asymmetric aldol reactions in organic solvents and in water were evaluated. Prolinamide phenols 1a-d were found to be effective catalysts for the reaction of aromatic aldehydes with cyclohexanone in neat ketone and in water. The anti-aldol products were obtained with up to 98/2 anti/syn ratio and 96% ee in neat ketone, 98/2 anti/syn ratio and 99% ee in water, respectively. (c) 2006 Elsevier Ltd. All rights reserved.