Journal of the American Chemical Society, volume 135, issue 1, pages 58-61

N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones

Lisa Candish ¹

David Lupton ¹

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School of Chemistry, Monash University, Clayton, Victoria 3800, Australia |

Publication type: Journal Article

Publication date: 2012-12-20

American Chemical Society (ACS)

Journal: Journal of the American Chemical Society

Quartile SCImago

Quartile WOS

Impact factor: 15

ISSN: 00027863, 15205126

DOI: 10.1021/ja310449k

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General Chemistry

Catalysis

Biochemistry

Colloid and Surface Chemistry

Abstract

The N-heterocyclic carbene (NHC)-catalyzed Claisen rearrangement of hybrid Ireland-Coates structures has been achieved, allowing the stereoselective synthesis of highly functionalized β-lactones. The reaction proceeds with high diastereoselectivity (>20:1) and affords a diverse range of β-lactone fused cyclopentanes. Mechanistic studies are detailed.

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Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry	Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 1, 0.63% Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 1 publication, 0.63%
Nature Reviews Chemistry	Nature Reviews Chemistry, 1, 0.63% Nature Reviews Chemistry 1 publication, 0.63%
Russian Chemical Bulletin	Russian Chemical Bulletin, 1, 0.63% Russian Chemical Bulletin 1 publication, 0.63%
Nature Communications	Nature Communications, 1, 0.63% Nature Communications 1 publication, 0.63%
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	5 10 15 20 25

Citations by publishers

	10 20 30 40 50 60 70
Wiley	Wiley, 66, 41.25% Wiley 66 publications, 41.25%
American Chemical Society (ACS)	American Chemical Society (ACS), 40, 25% American Chemical Society (ACS) 40 publications, 25%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 28, 17.5% Royal Society of Chemistry (RSC) 28 publications, 17.5%
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Springer Nature	Springer Nature, 6, 3.75% Springer Nature 6 publications, 3.75%
Thieme	Thieme, 3, 1.88% Thieme 3 publications, 1.88%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 2, 1.25% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 2 publications, 1.25%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 0.63% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 0.63%
Society of Synthetic Organic Chemistry	Society of Synthetic Organic Chemistry, 1, 0.63% Society of Synthetic Organic Chemistry 1 publication, 0.63%
King Saud University	King Saud University, 1, 0.63% King Saud University 1 publication, 0.63%
	10 20 30 40 50 60 70

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Candish L., Lupton D. N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones // Journal of the American Chemical Society. 2012. Vol. 135. No. 1. pp. 58-61.

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RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/ja310449k

UR - https://doi.org/10.1021/ja310449k

TI - N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones

T2 - Journal of the American Chemical Society

AU - Candish, Lisa

AU - Lupton, David

PY - 2012

DA - 2012/12/20 00:00:00

PB - American Chemical Society (ACS)

SP - 58-61

IS - 1

VL - 135

SN - 0002-7863

SN - 1520-5126

ER -

BibTex |

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BibTex Copy

@article{2012_Candish,

author = {Lisa Candish and David Lupton},

title = {N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones},

journal = {Journal of the American Chemical Society},

year = {2012},

volume = {135},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/ja310449k},

number = {1},

pages = {58--61},

doi = {10.1021/ja310449k}

}

MLA

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MLA Copy

Candish, Lisa, and David Lupton. “N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones.” Journal of the American Chemical Society, vol. 135, no. 1, Dec. 2012, pp. 58-61. https://doi.org/10.1021/ja310449k.

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)