Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, China.
Chem Commun (Camb). 2018 May 1;54(36):4581-4584. doi: 10.1039/c8cc02097c.
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.
尽管在将 SCF3 功能引入各种分子方面取得了最近的进展，但对映选择性三氟甲基化仍然具有挑战性，特别是羰基化合物的α-三氟甲基化。本研究描述了一种非环烯酮的 Cu 催化的对映选择性串联 1,4-加成/三氟甲基化反应。该串联反应能够使-SCF3 基团不对称地整合到羰基化合物中，在 50-92%的收率下建立手性叔碳中心，并提供 α-SCF3-β-取代的羰基化合物，对映选择性高达 20 : 1 dr 和 96% ee。
