Asymmetric Synthesis of β-Hydroxy Sulfides Controlled by Remote Sulfoxides

摘要

Reactions of (S)-α-(methylthio)-2-(p-tolylsulfinyl)benzyl car-banion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of β-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselectivity depends on steric factors (from 20% to > 98% de).