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Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines
Journal article   Open access

Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines

Xiao Zhou, Yongwei Wu and Li Deng
Journal of the American Chemical Society, Vol.138(37), pp.12297-12302
09/21/2016
PMCID: PMC5072400
PMID: 27579574

Abstract

Fluorocarbons - chemistry Protons Molecular Structure Catalysis Betaine - analogs & derivatives Imines - chemistry Reaction mechanisms Amines Stereoselectivity Catalysts Isomerization Organic Chemistry
We have developed a new class of cinchonium betaine catalysts bearing both a base moiety and an aromatic moiety as an N-substituent of the quinuclidine motif. These cinchonium betaines were found to promote proton transfer catalysis with 1000-5000 turnovers per 24 h, thereby enabling us to realize highly efficient enantioselective isomerization of trifluoromethyl imines to provide a practical access to optically active trifluoromethylated amines.
url
https://doi.org/10.1021/jacs.6b08727View
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