Highly stereoselective additions of sulfur stabilized carbanions to [(S)R]-2-(p-tolylsulfinyl)cyclohexanones

We describe the addition reactions of alpha -thiocarbanions derived from su lfoxides, thioethers, and sulfones to 2-(p-tolysulfinyl)cyclohexanones. The high stereoselectivity observed in the formation of the chiral hydroxylic carbon is controlled by the configuration of the sulfinyl group at the subs trate, but it is modulated by the nature of the sulfur function at the reag ent (SOTol>SO2Ph>SPh). The highly stereoselective formation of the second s tereogenic center generated in these reactions from prochiral anions is onl y achieved with sulfinylcarbanions, the configuration of which controls tha t of such a center. (C) 2000 Elsevier Science Ltd. All rights reserved.