Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones

Xiaoyu Chen, David Philip Day, Wan Teng Teo, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)

Abstract

A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.

Original languageEnglish
Pages (from-to)5936-5939
Number of pages4
JournalOrganic Letters
Volume18
Issue number22
DOIs
Publication statusPublished - 18 Nov 2016

Cite this

@article{253ff6105c76469ab28167524f50a06f,
title = "Gold- and Br{\o}nsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones",
abstract = "A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Br{\o}nsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.",
author = "Xiaoyu Chen and Day, {David Philip} and Teo, {Wan Teng} and Chan, {Philip Wai Hong}",
year = "2016",
month = "11",
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doi = "10.1021/acs.orglett.6b03049",
language = "English",
volume = "18",
pages = "5936--5939",
journal = "Organic Letters",
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publisher = "American Chemical Society",
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Gold- and Brønsted Acid-Catalyzed Cycloisomerization of 1,8-Diynyl Vinyl Acetates to Bicyclo[2.2.1]hept-2-en-7-ones. / Chen, Xiaoyu; Day, David Philip; Teo, Wan Teng; Chan, Philip Wai Hong.

In: Organic Letters, Vol. 18, No. 22, 18.11.2016, p. 5936-5939.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Chen, Xiaoyu

AU - Day, David Philip

AU - Teo, Wan Teng

AU - Chan, Philip Wai Hong

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AB - A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.

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DO - 10.1021/acs.orglett.6b03049

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JO - Organic Letters

JF - Organic Letters

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