Asymmetric Synthesis of Secondary Alcohols and 1,2-Disubstituted Epoxides via Organocatalytic Sulfenylation.

Enantioenriched secondary alcohols can be prepared via a short reaction sequence involving asymmetric organocatalytic sulfenylation of an aldehyde, organometallic addition, and desulfurization. This process provides access to enantioenriched alcohols with sterically similar groups attached to the alcohol carbon atom. The intermediate β-hydroxysulfides can also serve as precursors to enantioenriched 1,2-disubstituted epoxides via alkylation of the sulfur and subsequent basemediated ring closure. [ABSTRACT FROM AUTHOR]