Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines
An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantiose...
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| Published in | ChemCatChem Vol. 12; no. 2; pp. 444 - 448 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
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Weinheim
Wiley Subscription Services, Inc
18.01.2020
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| Online Access | Get full text |
| ISSN | 1867-3880 1867-3899 |
| DOI | 10.1002/cctc.201901677 |
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| Abstract | An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.
Phosphine catalysis: Under 0.1 mol % of phosphonium salt catalyst, vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines has been developed. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products. |
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| AbstractList | An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products.
Phosphine catalysis: Under 0.1 mol % of phosphonium salt catalyst, vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines has been developed. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products. An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products. An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N ‐Boc isatin imines catalysed by amide phosphonium salt is described. This method allows the formation of intriguing adducts bearing both 3‐aminooxindole and coumarin moieties in excellent yields with excellent enantioselectivities. The utility of this method was illustrated by a gram scale synthesis using as low as 0.1 mol % of catalyst without chromatographic purification, and removal of the Boc protecting groups on the primary amine functionality in Mannich products. |
| Author | Zhang, Shuo Cao, Weiguo Wang, Chenghan Wu, Xiaoyu Wang, Jing Chen, Jie Ding, Weizhong |
| Author_xml | – sequence: 1 givenname: Jing surname: Wang fullname: Wang, Jing organization: Shanghai University – sequence: 2 givenname: Shuo surname: Zhang fullname: Zhang, Shuo organization: Shanghai University – sequence: 3 givenname: Weizhong surname: Ding fullname: Ding, Weizhong organization: Shanghai University – sequence: 4 givenname: Chenghan surname: Wang fullname: Wang, Chenghan organization: Shanghai University – sequence: 5 givenname: Jie surname: Chen fullname: Chen, Jie organization: Shanghai University – sequence: 6 givenname: Weiguo surname: Cao fullname: Cao, Weiguo email: wgcao@shu.edu.cn organization: Shanghai University – sequence: 7 givenname: Xiaoyu orcidid: 0000-0001-7179-4280 surname: Wu fullname: Wu, Xiaoyu email: wuxy@shu.edu.cn organization: Shanghai University |
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| Snippet | An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N‐Boc isatin imines catalysed by amide phosphonium salt is described. This... An asymmetric vinylogous Mannich reaction between 3‐cyano‐4‐methylcoumarins and N ‐Boc isatin imines catalysed by amide phosphonium salt is described. This... |
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| StartPage | 444 |
| SubjectTerms | Adducts Asymmetric Coumarin Enantiomers Imines Mannich reaction Oxindole Vinylogous |
| Title | Amide‐phosphonium Salt Catalyzed Enantioselective Vinylogous Mannich Addition of Coumarins to Isatin Imines |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fcctc.201901677 https://www.proquest.com/docview/2343422385 |
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