Asymmetric H2O-Nucleophilic Ring Opening of D-A Cyclopropanes: Catalyst Serves as a Source of Water

Qi Kai Kang; Lijia Wang; Qiong Jie Liu; Jun Fang Li; Yong Tang

doi:10.1021/jacs.5b10310

Asymmetric H₂O-Nucleophilic Ring Opening of D-A Cyclopropanes: Catalyst Serves as a Source of Water

Qi Kai Kang
, Lijia Wang
, Qiong Jie Liu
, Jun Fang Li
, Yong Tang^*

^*此作品的通讯作者

CAS - Shanghai Institute of Organic Chemistry
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

科研成果: 期刊稿件 › 文章 › 同行评审

89 引用（Scopus）

摘要

The first catalytic enantioselective ring-opening reaction of donor-acceptor cyclopropanes with water is described. By employing Cy-TOX/Cu(II) as catalyst, the reaction performed very well over a broad range of substrates, leading to the ring-opening products in 70-96% yields with up to 95% ee under mild conditions. The current method provides a new approach to direct access to γ-substituted GBH derivatives very efficiently. Importantly, Cu(ClO₄)₂·6H₂O proves to serve as both a Lewis acid and a source of water, which affords a fine system to controllably release water as a nucleophile in the asymmetric catalysis.

源语言	英语
页（从-至）	14594-14597
页数	4
期刊	Journal of the American Chemical Society
卷	137
期	46
DOI	https://doi.org/10.1021/jacs.5b10310
出版状态	已出版 - 25 11月 2015
已对外发布	是

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title = "Asymmetric H2O-Nucleophilic Ring Opening of D-A Cyclopropanes: Catalyst Serves as a Source of Water",

abstract = "The first catalytic enantioselective ring-opening reaction of donor-acceptor cyclopropanes with water is described. By employing Cy-TOX/Cu(II) as catalyst, the reaction performed very well over a broad range of substrates, leading to the ring-opening products in 70-96\% yields with up to 95\% ee under mild conditions. The current method provides a new approach to direct access to γ-substituted GBH derivatives very efficiently. Importantly, Cu(ClO4)2·6H2O proves to serve as both a Lewis acid and a source of water, which affords a fine system to controllably release water as a nucleophile in the asymmetric catalysis.",

author = "Kang, \{Qi Kai\} and Lijia Wang and Liu, \{Qiong Jie\} and Li, \{Jun Fang\} and Yong Tang",

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AU - Kang, Qi Kai

AU - Wang, Lijia

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AU - Li, Jun Fang

AU - Tang, Yong

PY - 2015/11/25

Y1 - 2015/11/25

N2 - The first catalytic enantioselective ring-opening reaction of donor-acceptor cyclopropanes with water is described. By employing Cy-TOX/Cu(II) as catalyst, the reaction performed very well over a broad range of substrates, leading to the ring-opening products in 70-96% yields with up to 95% ee under mild conditions. The current method provides a new approach to direct access to γ-substituted GBH derivatives very efficiently. Importantly, Cu(ClO4)2·6H2O proves to serve as both a Lewis acid and a source of water, which affords a fine system to controllably release water as a nucleophile in the asymmetric catalysis.

AB - The first catalytic enantioselective ring-opening reaction of donor-acceptor cyclopropanes with water is described. By employing Cy-TOX/Cu(II) as catalyst, the reaction performed very well over a broad range of substrates, leading to the ring-opening products in 70-96% yields with up to 95% ee under mild conditions. The current method provides a new approach to direct access to γ-substituted GBH derivatives very efficiently. Importantly, Cu(ClO4)2·6H2O proves to serve as both a Lewis acid and a source of water, which affords a fine system to controllably release water as a nucleophile in the asymmetric catalysis.

UR - https://www.scopus.com/pages/publications/84948652573

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DO - 10.1021/jacs.5b10310

M3 - 文章

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SP - 14594

EP - 14597

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 46

ER -

Asymmetric H2O-Nucleophilic Ring Opening of D-A Cyclopropanes: Catalyst Serves as a Source of Water

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Asymmetric H₂O-Nucleophilic Ring Opening of D-A Cyclopropanes: Catalyst Serves as a Source of Water