Issue 52, 2015
From the journal:

Chemical Communications

Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality†

Jianlin Zhang,a   Yulong Zhang,a   Lili Lin,a   Qian Yao,a   Xiaohua Liua  and  Xiaoming Feng*ab  

* Corresponding authors

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

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

Abstract

The catalytic asymmetric Michael addition/desymmetrization reaction of N-(2-t-butylphenyl)maleimides with unprotected 3-substituted-2-oxindoles was successfully realized using a chiral N,N′-dioxide-Sc(III) complex, leading to succinimides with two kinds of stereogenic elements—atom chirality and axial chirality—in up to 99% yield, 99% ee and >19 : 1 d.r.

Graphical abstract: Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality

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Article information

DOI
https://doi.org/10.1039/C5CC03203B
Article type
Communication
Submitted
17 Apr 2015
Accepted
19 May 2015
First published
04 Jun 2015

Chem. Commun., 2015,51, 10554-10557

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Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality

J. Zhang, Y. Zhang, L. Lin, Q. Yao, X. Liu and X. Feng, Chem. Commun., 2015, 51, 10554 DOI: 10.1039/C5CC03203B

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