N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines

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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Main Authors: Wang, Ming, Huang, Zhijian, Xu, Jianfeng, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/104218
http://hdl.handle.net/10220/19444
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Institution: Nanyang Technological University
Language: English
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spelling 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.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle 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

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