Issue 6, 2013
From the journal:

RSC Advances

Enantioselective synthesis of 2-substituted pyrrolidinesvia domino cross metathesis/intramolecular aza-Michael addition†

Hanbin Liu,a   Chuanqi Zeng,a   Jiajia Guo,a   Mengyao Zhanga  and  Shouyun Yu*a  

* Corresponding authors

a State Key Laboratory of Analytical Chemistry for Life Science, Institute of Chemical Biology and Drug Innovation, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing 210093, China
E-mail: yushouyun@nju.edu.cn
Web: http://hysz.nju.edu.cn/yusy

Abstract

A highly enantioselective intramolecular aza-Michael addition with enone carbamates catalyzed by chiral Brønsted acids was developed. A domino cross metathesis/aza-Michael addition for the preparation of 2-substituted pyrrolidines or benzopyrrolidines was also explored. The reactions described here provide an efficient asymmetric protocol for enantio-enriched heterocycles, especially 2-substituted pyrrolidines.

Graphical abstract: Enantioselective synthesis of 2-substituted pyrrolidines via domino cross metathesis/intramolecular aza-Michael addition

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Article information

DOI
https://doi.org/10.1039/C2RA22374K
Article type
Communication
Submitted
02 Oct 2012
Accepted
29 Nov 2012
First published
04 Dec 2012

RSC Adv., 2013,3, 1666-1668

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Enantioselective synthesis of 2-substituted pyrrolidines via domino cross metathesis/intramolecular aza-Michael addition

H. Liu, C. Zeng, J. Guo, M. Zhang and S. Yu, RSC Adv., 2013, 3, 1666 DOI: 10.1039/C2RA22374K

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