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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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-01, Vol.136 (4), p.1214-1217
Main Authors: Wang, Ming, Huang, Zhijian, Xu, Jianfeng, Chi, Yonggui Robin
Format: Article
Language:English
Subjects:
Azo Compounds - chemistry
Catalysis
Cyclization
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Imines - chemistry
Kinetics
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Thiosemicarbazones - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja411110f