N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines.J Am Chem Soc. 2014 Jan 29; 136(4):1214-7.JA
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.
Links
MeSH
Pub Type(s)
Journal Article
Research Support, Non-U.S. Gov't
Language
eng
PubMed ID
24422593
Citation
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, 2014, pp. 1214-7.
Wang M, Huang Z, Xu J, et al. N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines. J Am Chem Soc. 2014;136(4):1214-7.
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), 1214-7. https://doi.org/10.1021/ja411110f
Wang M, et al. N-heterocyclic Carbene-catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines. J Am Chem Soc. 2014 Jan 29;136(4):1214-7. PubMed PMID: 24422593.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - N-heterocyclic carbene-catalyzed [3+4] cycloaddition and kinetic resolution of azomethine imines.
AU - Wang,Ming,
AU - Huang,Zhijian,
AU - Xu,Jianfeng,
AU - Chi,Yonggui Robin,
Y1 - 2014/01/16/
PY - 2014/1/16/entrez
PY - 2014/1/16/pubmed
PY - 2014/9/24/medline
SP - 1214
EP - 7
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 136
IS - 4
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.
SN - 1520-5126
UR - https://www.unboundmedicine.com/medline/citation/24422593/N_heterocyclic_carbene_catalyzed_[3+4]_cycloaddition_and_kinetic_resolution_of_azomethine_imines_
DB - PRIME
DP - Unbound Medicine
ER -
