Issue 19, 2011
From the journal:

Chemical Communications

Morita–Baylis–Hillman adducts as effective dipolarophiles in Copper(i)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides: asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center†

Huai-Long Teng,a   He Huang,a   Hai-Yan Taoa  and  Chun-Jiang Wang*ab  

* Corresponding authors

a College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China
E-mail: cjwang@whu.edu.cn
Fax: 86-27-68754067

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 354 Fenglin Road, Shanghai 200032, China

Abstract

The first catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with easily accessible Morita–Baylis–Hillman adducts as the dipolarophiles has been developed successfully and provides the highly substituted pyrrolidines bearing a unique quaternary and two tertiary stereogenic centers in excellent diastereoselectivity and up to 97% ee.

Graphical abstract: Morita–Baylis–Hillman adducts as effective dipolarophiles in Copper(i)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides : asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center

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Article information

DOI
https://doi.org/10.1039/C1CC11138H
Article type
Communication
Submitted
25 Feb 2011
Accepted
21 Mar 2011
First published
08 Apr 2011

Chem. Commun., 2011,47, 5494-5496

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Morita–Baylis–Hillman adducts as effective dipolarophiles in Copper(I)-catalyzed 1,3-dipolar cycloaddition with azomethine ylides: asymmetric construction of pyrrolidine derivatives containing quaternary stereogenic center

H. Teng, H. Huang, H. Tao and C. Wang, Chem. Commun., 2011, 47, 5494 DOI: 10.1039/C1CC11138H

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