Copper-catalyzed desymmetrization of prochiral 4,4-disubstituted cyclopentenes via a site-selective allylic oxidation: a concise total synthesis of untenone A

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成果类型：

期刊论文

作者：

Gui, Qingwen;Wang, JuanJuan;Ng, Sean;Dancevic, Anja;Wright, Timothy B.;...

通讯作者：

Evans, P. Andrew

作者机构：

[Wang, JuanJuan; Gui, Qingwen; Wright, Timothy B.; Evans, P. Andrew] Queens Univ, Dept Chem, 90 Bader Lane, Kingston, ON K7L 3N6, Canada.

[Gui, Qingwen] Hunan Agr Univ, Coll Sci, Changsha 410128, Hunan, Peoples R China.

[Wang, JuanJuan] Henan Polytech Univ, Coll Chem & Chem Engn, Jiaozuo 45400, Henan, Peoples R China.

[Ng, Sean; Dancevic, Anja] Univ Liverpool, Dept Chem, Crown St, Liverpool L69 7ZD, Merseyside, England.

通讯机构：

[Evans, P. Andrew] Q

Queens Univ, Dept Chem, 90 Bader Lane, Kingston, ON K7L 3N6, Canada.

语种：

英文

期刊：

Chemical Communications

ISSN：

1359-7345

年：

2019

卷：

期：

页码：

12368-12371

DOI：

10.1039/c9cc01743g

基金类别：

NSERCNatural Sciences and Engineering Research Council of Canada (NSERC); Tier 1 Canada Research ChairCanada Research Chairs; National Natural Science Foundation of ChinaNational Natural Science Foundation of China (NSFC) [21502044, 201506130048]; EPSRCUK Research & Innovation (UKRI)Engineering & Physical Sciences Research Council (EPSRC); Syngenta (Bracknell)

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本校为其他机构

院系归属：

理学院

摘要：

The desymmetrization of prochiral 4,4-disubstituted cyclopentenes via a site-selective copper-catalyzed allylic oxidation is described. This study provides a direct comparison of a series of known methods for allylic oxidation, and thus identifies ligand-free copper(i) iodide as the optimal catalyst for this particular process. Notably, this work offers a convenient approach to the preparation of γ-quaternary α,β-unsaturated cyclopentenones, which permits an efficient three-step total synthesis...

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Copper-catalyzed desymmetrization of prochiral 4,4-disubstituted cyclopentenes via a site-selective allylic oxidation: a concise total synthesis of untenone A

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