Chemoselective Reduction of α,β-Unsaturated Carbonyl Compounds via a CS 2 / t- BuOK System: Dimethyl Sulfoxide as a Hydrogen Source.

A novel and practical approach to access saturated ketones from unsaturated ketone derivatives via a CS 2 / t- BuOK system in dimethyl sulfoxide (DMSO) is reported. The in situ generation of xanthate salt through the reaction of carbon disulfide and potassium tert -butoxide is essential to this transformation. Deuterium-labeling experiments demonstrated that DMSO can act as a hydrogen donor.