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

Ming Yu Jin, Juncheng Li, Renke Huang, Yuxuan Zhou, Lung Wa Chung, Jun (Joelle) Wang

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)4581-4584
Number of pages4
JournalChemical Communications
Volume54
Issue number36
DOIs
Publication statusPublished - 4 May 2018

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