N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines
The first N-heterocyclic carbene (NHC)-catalyzed [3+4] cycloaddition of azomethine imines and enals is disclosed. Oxidative catalytic remote activation of enals affords 1,4-dipolarophile intermediates that react with 1,3-dipolar azomethine imines to generate dinitrogen-fused seven-membered heterocyc...
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sg-ntu-dr.10356-1042182020-03-07T12:34:58Z N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines Wang, Ming Huang, Zhijian Xu, Jianfeng Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry The first N-heterocyclic carbene (NHC)-catalyzed [3+4] cycloaddition of azomethine imines and enals is disclosed. Oxidative catalytic remote activation of enals affords 1,4-dipolarophile intermediates that react with 1,3-dipolar azomethine imines to generate dinitrogen-fused seven-membered heterocyclic products with high optical purities. Our approach also provides effective kinetic resolution of azomethine imines, in which the substrate chiral center that is remote from the NHC catalyst can be well resolved. 2014-05-26T02:10:50Z 2019-12-06T21:28:34Z 2014-05-26T02:10:50Z 2019-12-06T21:28:34Z 2014 2014 Journal Article Wang, M., Huang, Z., Xu, J., & Chi, Y. R. (2014). N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines. Journal of the American Chemical Society, 136(4), 1214–1217. 0002-7863 https://hdl.handle.net/10356/104218 http://hdl.handle.net/10220/19444 10.1021/ja411110f 179788 en Journal of the American Chemical Society © 2014 American Chemical Society. |
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DRNTU::Science::Chemistry::Organic chemistry Wang, Ming Huang, Zhijian Xu, Jianfeng Chi, Robin Yonggui N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| description |
The first N-heterocyclic carbene (NHC)-catalyzed [3+4] cycloaddition of azomethine imines and enals is disclosed. Oxidative catalytic remote activation of enals affords 1,4-dipolarophile intermediates that react with 1,3-dipolar azomethine imines to generate dinitrogen-fused seven-membered heterocyclic products with high optical purities. Our approach also provides effective kinetic resolution of azomethine imines, in which the substrate chiral center that is remote from the NHC catalyst can be well resolved. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Wang, Ming Huang, Zhijian Xu, Jianfeng Chi, Robin Yonggui |
| format |
Article |
| author |
Wang, Ming Huang, Zhijian Xu, Jianfeng Chi, Robin Yonggui |
| author_sort |
Wang, Ming |
| title |
N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| title_short |
N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| title_full |
N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| title_fullStr |
N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| title_full_unstemmed |
N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| title_sort |
n-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines |
| publishDate |
2014 |
| url |
https://hdl.handle.net/10356/104218 http://hdl.handle.net/10220/19444 |
| _version_ |
1681034645330722816 |