Catalytic asymmetric trifluoromethylthiolation of carbonyl compounds via a diastereo and enantioselective Cu-catalyzed tandem reaction

Abstract

Although recent progress has been made in introducing an SCF₃ functionality into a variety of molecules, enantioselective trifluoromethylthiolation remains challenging, especially the α-trifluoromethylthiolation of carbonyl compounds. The present study describes a diastereo and enantioselective Cu-catalyzed tandem 1,4-addition/trifluoromethylthiolation of acyclic enones. The tandem reaction enables the asymmetric integration of the –SCF₃ group to carbonyl compounds, establishing chiral tertiary α-carbon centers and affording α-SCF₃-β-substituted carbonyl compounds in 50–92% yields with up to 20 : 1 dr and 96% ee.