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...
| Main Authors: | , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
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2014
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| Online Access: | https://hdl.handle.net/10356/101214 http://hdl.handle.net/10220/19802 |
| _version_ | 1826115735414374400 |
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| author | Chen, Wenchao Jing, Zhengzhong Chin, Kek Foo Qiao, Baokun Zhao, Yan Yan, Lin Tan, Choon-Hong Jiang, Zhiyong |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Chen, Wenchao Jing, Zhengzhong Chin, Kek Foo Qiao, Baokun Zhao, Yan Yan, Lin Tan, Choon-Hong Jiang, Zhiyong |
| author_sort | Chen, Wenchao |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T04:00:02Z |
| format | Journal Article |
| id | ntu-10356/101214 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:00:02Z |
| publishDate | 2014 |
| record_format | dspace |
| spelling | ntu-10356/1012142020-03-07T12:37:05Z 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::Organic synthesis 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. 2014-06-17T02:34:41Z 2019-12-06T20:35:17Z 2014-06-17T02:34:41Z 2019-12-06T20:35:17Z 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/10356/101214 http://hdl.handle.net/10220/19802 10.1002/adsc.201301027 en Advanced synthesis & catalysis © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis 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 |
| title | 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_short | 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 |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | https://hdl.handle.net/10356/101214 http://hdl.handle.net/10220/19802 |
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