Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide

Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane‐based bifunctional chiral sulfide catalyst and a shelf‐stable electrophi...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-05, Vol.55 (19), p.5846-5850
Main Authors: Liu, Xiang, An, Rui, Zhang, Xuelin, Luo, Jie, Zhao, Xiaodan
Format: Article
Language:English
Subjects:
alkenes
asymmetric catalysis
chiral sulfides
organocatalysis
trifluoromethylthiolation
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Summary:Enantioselective trifluoromethylthiolation, especially of alkenes, is a challenging task. In this work, we have developed an efficient approach for enantioselective trifluoromethylthiolating lactonization by designing an indane‐based bifunctional chiral sulfide catalyst and a shelf‐stable electrophilic SCF3 reagent. The desired products were formed with diastereoselectivities of >99:1 and good to excellent enantioselectivities. The transformation represents the first enantioselective trifluoromethylthiolation of alkenes and the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center. An efficient approach for enantioselective trifluoromethylthiolating lactonization entails the use of an indane‐based bifunctional chiral sulfide catalyst and a new shelf‐stable electrophilic SCF3 reagent. This transformation represents the first enantioselective trifluoromethylthiolation that is enabled by a catalyst with a Lewis basic sulfur center.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201601713