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Enantioselective Electrophilic Trifluoromethylthiolation of β-Ketoesters: A Case of Reactivity and Selectivity Bias for Orga...

by Xianwei Wang, Tao Yang, Xiaolin Cheng, Qilong Shen
Publication Type
Journal
Journal Name
Angewandte Chemie International Edition
Publication Date
Page Numbers
12860 to 12864
Volume
52
Issue
49

A chiral Lewis base or a phase-transfer catalyst (PTC) can mediate the highly enantioselective trifluoromethylthiolation of β-ketoesters with the previously developed SCF3 reagent (see scheme). Reactions of indanone-derived β-ketoesters occurred with high yield and excellent enantioselectivity with quinine as catalyst. Reactions of tetralone- or 1-benzosuberone-derived β-ketoesters occurred with moderate to good enantioselectivity with a quinine-derived PTC.