Issue 4, 2016
From the journal:

Chemical Science

Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene†

Jing Guo,a   Yangbin Liu,a   Xiangqiang Li,a   Xiaohua Liu,*a   Lili Lina  and  Xiaoming Feng*ab  

* Corresponding authors

a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China
E-mail: liuxh@scu.edu.cn, xmfeng@scu.edu.cn
Fax: +86 28 85418249
Tel: +86 28 85418249

b Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China

Abstract

A chiral Lewis acid-promoted enantioselective cyclopropanation using phenyliodonium ylide as the carbene precursor was developed. A variety of spirocyclopropane-oxindoles with contiguous tertiary and all carbon quaternary centers were obtained in excellent outcomes (up to 99% yield, >19 : 1 d.r., up to 99% ee). EPR spectroscopy study supported a stepwise biradical mechanism.

Graphical abstract: Nickel(ii)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene

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Article information

DOI
https://doi.org/10.1039/C5SC03658E
Article type
Edge Article
Submitted
26 Sep 2015
Accepted
03 Jan 2016
First published
04 Jan 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2016,7, 2717-2721

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Nickel(II)-catalyzed enantioselective cyclopropanation of 3-alkenyl-oxindoles with phenyliodonium ylide via free carbene

J. Guo, Y. Liu, X. Li, X. Liu, L. Lin and X. Feng, Chem. Sci., 2016, 7, 2717 DOI: 10.1039/C5SC03658E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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