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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sg-ntu-dr.10356-1009932020-03-07T12:34:52Z Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols Chen, Wenchao Jing, Zhengzhong Chin, Kek Foo Qiao, Baokun Zhao, Yan Yan, Lin Tan, Choon-Hong Jiang, Zhiyong School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry 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. 2014-06-12T06:08:29Z 2019-12-06T20:31:48Z 2014-06-12T06:08:29Z 2019-12-06T20:31:48Z 2014 2014 Journal Article Chen, W., Jing, Z., Chin, K. F., Qiao, B., Zhao, Y., Yan, L., et al. (2014). Catalytic Asymmetric Conjugate Addition of Mercaptans to β-Substituted-β-Trifluoromethyl Oxazolidinone Enoates: Access to Chiral Trifluoromethylated Tertiary Thioethers and Thiols. Advanced Synthesis & Catalysis, 356(6), 1292-1300. 1615-4150 https://hdl.handle.net/10356/100993 http://hdl.handle.net/10220/19696 10.1002/adsc.201301027 en Advanced synthesis & catalysis © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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DRNTU::Science::Chemistry::Organic chemistry Chen, Wenchao Jing, Zhengzhong Chin, Kek Foo Qiao, Baokun Zhao, Yan Yan, Lin Tan, Choon-Hong Jiang, Zhiyong Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
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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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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Chen, Wenchao Jing, Zhengzhong Chin, Kek Foo Qiao, Baokun Zhao, Yan Yan, Lin Tan, Choon-Hong Jiang, Zhiyong |
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Article |
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Chen, Wenchao Jing, Zhengzhong Chin, Kek Foo Qiao, Baokun Zhao, Yan Yan, Lin Tan, Choon-Hong Jiang, Zhiyong |
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Chen, Wenchao |
title |
Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
title_short |
Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
title_full |
Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
title_fullStr |
Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
title_full_unstemmed |
Catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
title_sort |
catalytic asymmetric conjugate addition of mercaptans to β-substituted-β-trifluoromethyl oxazolidinone enoates: access to chiral trifluoromethylated tertiary thioethers and thiols |
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2014 |
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https://hdl.handle.net/10356/100993 http://hdl.handle.net/10220/19696 |
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1681045325587939328 |