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Enantioselective Electrophilic Trifluoromethylthiolation of β‐Ketoesters: A Case of Reactivity and Selectivity Bias for Organocatalysis
Author(s) -
Wang Xueqiang,
Yang Tao,
Cheng Xiaolin,
Shen Qilong
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201305075
Subject(s) - enantioselective synthesis , chemistry , electrophile , organocatalysis , reagent , catalysis , yield (engineering) , reactivity (psychology) , cinchonidine , selectivity , combinatorial chemistry , squaramide , organic chemistry , cinchona , materials science , medicine , alternative medicine , pathology , metallurgy
A chiral Lewis base or a phase‐transfer catalyst (PTC) can mediate the highly enantioselective trifluoromethylthiolation of β‐ketoesters with the previously developed SCF 3 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.