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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

88 Scopus citations

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.

Original language	English
Pages (from-to)	14594-14597
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	46
DOIs	https://doi.org/10.1021/jacs.5b10310
State	Published - 25 Nov 2015
Externally published	Yes

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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",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

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doi = "10.1021/jacs.5b10310",

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T1 - Asymmetric H2O-Nucleophilic Ring Opening of D-A Cyclopropanes

T2 - Catalyst Serves as a Source of Water

AU - Kang, Qi Kai

AU - Wang, Lijia

AU - Liu, Qiong Jie

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

U2 - 10.1021/jacs.5b10310

DO - 10.1021/jacs.5b10310

M3 - 文章

AN - SCOPUS:84948652573

SN - 0002-7863

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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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