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

Ming Wang; Zhijian Huang; Jianfeng Xu; Yonggui Robin Chi

doi:10.1021/ja411110f

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

Ming Wang, Zhijian Huang, Jianfeng Xu, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

234 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1214-1217
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	4
DOIs	https://doi.org/10.1021/ja411110f
Publication status	Published - Jan 29 2014
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "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.",

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AU - Wang, Ming

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AU - Chi, Yonggui Robin

PY - 2014/1/29

Y1 - 2014/1/29

N2 - 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.

AB - 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.

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

Abstract

ASJC Scopus Subject Areas

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