Chemoselective Reduction of & alpha;,& beta;-Unsaturated Carbonyl Compounds via a CS2/t-BuOK System: Dimethyl Sulfoxide as a Hydrogen Source

A novel and practical approach to access saturated ketonesfromunsaturated ketone derivatives via a CS2/t-BuOK system in dimethyl sulfoxide (DMSO) is reported. The in situ generation of xanthate salt through the reactionof carbon disulfide and potassium tert-butoxide isessential to this transformation. Deuterium-labeling experiments demonstratedthat DMSO can act as a hydrogen donor.

Automated summary

A novel and practical method for accessing saturated ketones from unsaturated ketone derivatives using a CS2/t-BuOK system in dimethyl sulfoxide (DMSO) is presented. The in situ generation of xanthate salt through the reaction of carbon disulfide and potassium tert-butoxide is crucial for this transformation. Deuterium-labeling experiments showed that DMSO can act as a hydrogen donor.