N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines
Publication type: Journal Article
Publication date: 2014-01-16
scimago Q1
wos Q1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
24422593
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
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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247
Total citations:
247
Citations from 2025:
8
(3.25%)
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GOST
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Wang M. et al. N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines // Journal of the American Chemical Society. 2014. Vol. 136. No. 4. pp. 1214-1217.
GOST all authors (up to 50)
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Wang M., Huang Z., Xu J., Chi Y. R. N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines // Journal of the American Chemical Society. 2014. Vol. 136. No. 4. pp. 1214-1217.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/ja411110f
UR - https://doi.org/10.1021/ja411110f
TI - N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines
T2 - Journal of the American Chemical Society
AU - Wang, Ming
AU - Huang, Zhijian
AU - Xu, Jianfeng
AU - Chi, Yonggui Robin
PY - 2014
DA - 2014/01/16
PB - American Chemical Society (ACS)
SP - 1214-1217
IS - 4
VL - 136
PMID - 24422593
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2014_Wang,
author = {Ming Wang and Zhijian Huang and Jianfeng Xu and Yonggui Robin Chi},
title = {N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines},
journal = {Journal of the American Chemical Society},
year = {2014},
volume = {136},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/ja411110f},
number = {4},
pages = {1214--1217},
doi = {10.1021/ja411110f}
}
Cite this
MLA
Copy
Wang, Ming, et al. “N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines.” Journal of the American Chemical Society, vol. 136, no. 4, Jan. 2014, pp. 1214-1217. https://doi.org/10.1021/ja411110f.