beta-Hydroxysulfoxides as chiral cyclic ketone equivalents: enantioselective synthesis of polysubstituted cyclohexanones, cyclohexenones and cyclohexenediones

Chem Commun (Camb). 2002 Dec 21:(24):3052-3. doi: 10.1039/b209121f.

Abstract

The beta-hydroxysulfoxide moiety, after oxidation to sulfone, acts as a masked carbonyl group in a cyclic system, opening an easy access to differently substituted enantiomerically pure cyclic ketones by means of aluminium-mediated conjugate additions, stereoselective reductions and elimination by retrocondensation in basic medium.