Journal of the American Chemical Society, volume 137, issue 25, pages 8006-8009

Asymmetric Annulation of Donor–Acceptor Cyclopropanes with Dienes

Hao Xu ¹

Jiang Lin Hu ¹

Lijia Wang ¹

Saihu Liao ¹

Yong Tang ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China |

Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China |

Publication type: Journal Article

Publication date: 2015-06-18

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor: 15

ISSN: 00027863, 15205126

DOI: 10.1021/jacs.5b04429

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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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Chemical Reviews	Chemical Reviews, 2, 1.09% Chemical Reviews 2 publications, 1.09%
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Trends in Chemistry	Trends in Chemistry, 1, 0.54% Trends in Chemistry 1 publication, 0.54%
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	5 10 15 20 25 30

Citations by publishers

	10 20 30 40 50 60 70 80 90
Wiley	Wiley, 84, 45.65% Wiley 84 publications, 45.65%
American Chemical Society (ACS)	American Chemical Society (ACS), 50, 27.17% American Chemical Society (ACS) 50 publications, 27.17%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 25, 13.59% Royal Society of Chemistry (RSC) 25 publications, 13.59%
Elsevier	Elsevier, 10, 5.43% Elsevier 10 publications, 5.43%
Thieme	Thieme, 5, 2.72% Thieme 5 publications, 2.72%
Springer Nature	Springer Nature, 3, 1.63% Springer Nature 3 publications, 1.63%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 2, 1.09% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 2 publications, 1.09%
Bentham Science	Bentham Science, 1, 0.54% Bentham Science 1 publication, 0.54%
The Royal Society	The Royal Society, 1, 0.54% The Royal Society 1 publication, 0.54%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 1, 0.54% Shanghai Institute of Organic Chemistry 1 publication, 0.54%
Oxford University Press	Oxford University Press, 1, 0.54% Oxford University Press 1 publication, 0.54%
	10 20 30 40 50 60 70 80 90

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GOST Copy

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) Copy

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.

RIS |

Cite this

RIS Copy

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 - Hu, Jiang Lin

AU - Xu, Hao

AU - Wang, Lijia

AU - Liao, Saihu

AU - Tang, Yong

PY - 2015

DA - 2015/06/18 00:00:00

PB - American Chemical Society (ACS)

SP - 8006-8009

IS - 25

VL - 137

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

Cite this

BibTex Copy

@article{2015_Xu,

author = {Jiang Lin Hu and Hao Xu 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}

}

MLA

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.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor

ISSN

00027863 (Print)
15205126 (Electronic)