Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines
Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade pro...
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| Published in | Angewandte Chemie Vol. 132; no. 42; pp. 18610 - 18614 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley Subscription Services, Inc
12.10.2020
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| Online Access | Get full text |
| ISSN | 0044-8249 1521-3757 |
| DOI | 10.1002/ange.202007352 |
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| Abstract | Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.
A protocol for Lewis acid‐catalyzed highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been developed. The reactions were catalyzed by chiral spiro‐bicyclic bisboranes and occurred under mild reaction conditions with high turnover numbers. |
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| AbstractList | Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations. Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations. A protocol for Lewis acid‐catalyzed highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been developed. The reactions were catalyzed by chiral spiro‐bicyclic bisboranes and occurred under mild reaction conditions with high turnover numbers. |
| Author | Liu, Ning Tian, Jun‐Jie Hu, Chen‐Yu Yang, Zhao‐Ying Tu, Xian‐Shuang Liang, Xin‐Shen Li, Xiang Wang, Xiao‐Chen |
| Author_xml | – sequence: 1 givenname: Jun‐Jie surname: Tian fullname: Tian, Jun‐Jie organization: Nankai University – sequence: 2 givenname: Zhao‐Ying surname: Yang fullname: Yang, Zhao‐Ying organization: Nankai University – sequence: 3 givenname: Xin‐Shen surname: Liang fullname: Liang, Xin‐Shen organization: Nankai University – sequence: 4 givenname: Ning surname: Liu fullname: Liu, Ning organization: Nankai University – sequence: 5 givenname: Chen‐Yu surname: Hu fullname: Hu, Chen‐Yu organization: Nankai University – sequence: 6 givenname: Xian‐Shuang surname: Tu fullname: Tu, Xian‐Shuang organization: Nankai University – sequence: 7 givenname: Xiang surname: Li fullname: Li, Xiang organization: Nankai University – sequence: 8 givenname: Xiao‐Chen orcidid: 0000-0001-5863-0804 surname: Wang fullname: Wang, Xiao‐Chen email: xcwang@nankai.edu.cn organization: Nankai University |
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| Snippet | Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The... |
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| SubjectTerms | asymmetric catalysis boron Catalysts Chemical reduction Chemistry Dihydropyridine Enantiomers heterocycles Heterocyclic compounds Hydroboration Natural products pyridine Pyridines Reagents reduction Substitutes |
| Title | Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines |
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