Preparation of highly optically pure homochiral sulfide-containing alcohols via oxazaborolidine-catalyzed asymmetric borane reduction of ketones.

Abstract

Highly optically pure homochiral 1-(4-alkylthiophenyl) alcohols were prepared efficiently and practically via the oxazaborolidine-catalyzed asymmetric borane reduction of prochiral ketones in toluene at 25 degrees C. The coordination of the sulfur atom in the ketones to the boron atom in the catalyst and borane can be inhibited under these reduction conditions.