Issue 44, 2015
From the journal:

Chemical Communications

The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides†

Wu-Lin Yang,a   Yang-Zi Liu,a   Shuai Luo,a   Xingxin Yu,*a   John S. Fosseyb  and  Wei-Ping Deng*a  

* Corresponding authors

a Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, People's Republic of China
E-mail: xxyu@ecust.edu.cn, weiping_deng@ecust.edu.cn

b School of Chemistry, University of Birmingham, Edgbaston, Birmingham, West Midlands, UK

Abstract

A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97% ee).

Graphical abstract: The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

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Article information

DOI
https://doi.org/10.1039/C5CC02362A
Article type
Communication
Submitted
20 Mar 2015
Accepted
28 Apr 2015
First published
28 Apr 2015

Chem. Commun., 2015,51, 9212-9215

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The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

W. Yang, Y. Liu, S. Luo, X. Yu, J. S. Fossey and W. Deng, Chem. Commun., 2015, 51, 9212 DOI: 10.1039/C5CC02362A

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