Journal of the American Chemical Society, volume 137, issue 25, pages 8006-8009
Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes
Publication type: Journal Article
Publication date: 2015-06-18
Q1
Q1
SJR: 5.489
CiteScore: 24.4
Impact factor: 14.4
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
An efficient [4 + 3] cycloaddition reaction of D-A cyclopropanes with dienes has been successfully developed. The reaction proceeds well with various dienolsilyl ethers in the presence of Lewis acid, delivering a variety of cycloheptenes and [n,5,0]carbobicycles with excellent stereoselectivity. The asymmetric version of this reaction is also realized using a newly designed chiral Cy-TOX ligand, providing a new approach to access optically active cycloheptenes and [n,5,0]carbobicycles. Mechanisic study reveals that the reaction involves a stepwise pathway, which undergoes an unusual ring opening of five-membered [3 + 2] intermediate and sequential intramolecular cyclization to afford the thermodynamically stable [4 + 3] annulation product.
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GOST
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Xu H. et al. Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes // Journal of the American Chemical Society. 2015. Vol. 137. No. 25. pp. 8006-8009.
GOST all authors (up to 50)
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Xu H., Hu J. L., Wang L., Liao S., Tang Y. Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes // Journal of the American Chemical Society. 2015. Vol. 137. No. 25. pp. 8006-8009.
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TY - JOUR
DO - 10.1021/jacs.5b04429
UR - https://doi.org/10.1021/jacs.5b04429
TI - Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes
T2 - Journal of the American Chemical Society
AU - Xu, Hao
AU - Hu, Jiang Lin
AU - Wang, Lijia
AU - Liao, Saihu
AU - Tang, Yong
PY - 2015
DA - 2015/06/18
PB - American Chemical Society (ACS)
SP - 8006-8009
IS - 25
VL - 137
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2015_Xu,
author = {Hao Xu and Jiang Lin Hu and Lijia Wang and Saihu Liao and Yong Tang},
title = {Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes},
journal = {Journal of the American Chemical Society},
year = {2015},
volume = {137},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/jacs.5b04429},
number = {25},
pages = {8006--8009},
doi = {10.1021/jacs.5b04429}
}
Cite this
MLA
Copy
Xu, Hao, et al. “Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes.” Journal of the American Chemical Society, vol. 137, no. 25, Jun. 2015, pp. 8006-8009. https://doi.org/10.1021/jacs.5b04429.