Issue 36, 2018

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
15 Mar 2018
Accepted
09 Apr 2018
First published
10 Apr 2018

Chem. Commun., 2018,54, 4581-4584

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

M. Y. Jin, J. Li, R. Huang, Y. Zhou, L. W. Chung and J. (. Wang, Chem. Commun., 2018, 54, 4581 DOI: 10.1039/C8CC02097C

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