Aldol Reaction Catalyzed by a Hydrophilic Catalyst in Aqueous Micelle as an Enzyme Mimic System

Chitosan-supported L-proline complex was synthesized and applied as a catalyst for the direct asymmetric aldol reaction in various organic solvents and water as well. It was found that the novel synthesized catalyst was able to efficiently catalyze the aldol reaction in various media. The catalytic capacity and stereo selectivity of the catalyst were obviously improved with the introduction of aqueous micelle, possibly because the micelle functioned as a hydrophobic pocket, like the hydrophobic portion in enzymes. Moreover, the present synthetic catalyst showed performance similar to that of enzymes and could be used as a model of enzyme catalysis to help better understand the mystic mechanism of enzymes. Chirality 21:492-496, 2009. (C) 2008 Wiley-Liss, Inc.