Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates : access to chiral trifluoromethylated tertiary thioethers and thiols

Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates : access to chiral trifluoromethylated tertiary thioethers and thiols

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 Cinch...

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Bibliographic Details
Main Authors: Chen, Wenchao, Jing, Zhengzhong, Chin, Kek Foo, Qiao, Baokun, Zhao, Yan, Yan, Lin, Tan, Choon-Hong, Jiang, Zhiyong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Online Access:https://hdl.handle.net/10356/101214
http://hdl.handle.net/10220/19802
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Institution: Nanyang Technological University
Language: English
Description
Summary: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.

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