Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates : access to chiral trifluoromethylated tertiary thioethers and thiols
Author
Chen, Wenchao
Jing, Zhengzhong
Chin, Kek Foo
Qiao, Baokun
Zhao, Yan
Yan, Lin
Tan, Choon-Hong
Jiang, Zhiyong
Date of Issue
2014School
School of Physical and Mathematical Sciences
Abstract
The first asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates has been developed. The opposite enantiomers of adducts, containing a trifluoromethylated hetero-quaternary stereogenic centers, could be obtained by utilizing two pseudo-enantiomeric Cinchona alkaloid-derived tertiary amine/squaramides as catalysts. Potassium dihydrogen phosphate was found to accelerate the reaction rate without compromising the enantioselective excess. A variety of chiral trifluoromethylated tertiary thioethers and thiols were readily prepared with excellent enantioselectivity.
Subject
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Type
Journal Article
Series/Journal Title
Advanced synthesis & catalysis
Rights
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Collections
http://dx.doi.org/10.1002/adsc.201301027
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