Issue 83, 2013
From the journal:

Chemical Communications

exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(i)/DTBM-BIPHEP†

Qing-Hua Li,a   Tang-Lin Liu,a   Liang Wei,a   Xiang Zhou,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, Shanghai, China

Abstract

An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98 : 2), excellent enantioselectivity (96–>99% ee) and a broad substrate scope under mild conditions.

Graphical abstract: exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(i)/DTBM-BIPHEP

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Article information

DOI
https://doi.org/10.1039/C3CC45493B
Article type
Communication
Submitted
19 Jul 2013
Accepted
22 Aug 2013
First published
23 Aug 2013

Chem. Commun., 2013,49, 9642-9644

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exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP

Q. Li, T. Liu, L. Wei, X. Zhou, H. Tao and C. Wang, Chem. Commun., 2013, 49, 9642 DOI: 10.1039/C3CC45493B

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