Angewandte Chemie - International Edition, volume 58, issue 17, pages 5739-5743
Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction
Publication type: Journal Article
Publication date: 2019-03-19
Q1
Q1
SJR: 5.300
CiteScore: 26.6
Impact factor: 16.1
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
Dearomatization of anthranils with vinylcyclopropanes (VCPs) by Pd-catalyzed [4+3] cyclization reaction has been realized. In the presence of a catalytic amount of borane as an activator, bridged cyclic products were obtained in good to excellent yields with excellent stereoselectivities. By introducing a chiral PHOX ligand (L5), asymmetric dearomatization reactions of anthranils with vinylcyclopropanes proceeded with excellent enantioselectivity. Borane plays a key role for the reactivity, likely owing to the formation of a borane-anthranil complex which has been confirmed by NMR experiments.
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Cheng Q. et al. Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction // Angewandte Chemie - International Edition. 2019. Vol. 58. No. 17. pp. 5739-5743.
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Cheng Q., Xie J., Weng Y. C., You S. Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction // Angewandte Chemie - International Edition. 2019. Vol. 58. No. 17. pp. 5739-5743.
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TY - JOUR
DO - 10.1002/anie.201901251
UR - https://doi.org/10.1002/anie.201901251
TI - Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction
T2 - Angewandte Chemie - International Edition
AU - Cheng, Qiang
AU - Xie, Jia-Hao
AU - Weng, Yue Cheng
AU - You, Shu-Li
PY - 2019
DA - 2019/03/19
PB - Wiley
SP - 5739-5743
IS - 17
VL - 58
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2019_Cheng,
author = {Qiang Cheng and Jia-Hao Xie and Yue Cheng Weng and Shu-Li You},
title = {Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction},
journal = {Angewandte Chemie - International Edition},
year = {2019},
volume = {58},
publisher = {Wiley},
month = {mar},
url = {https://doi.org/10.1002/anie.201901251},
number = {17},
pages = {5739--5743},
doi = {10.1002/anie.201901251}
}
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Cheng, Qiang, et al. “Pd‐Catalyzed Dearomatization of Anthranils with Vinylcyclopropanes by [4+3] Cyclization Reaction.” Angewandte Chemie - International Edition, vol. 58, no. 17, Mar. 2019, pp. 5739-5743. https://doi.org/10.1002/anie.201901251.