Issue 1, 2017
From the journal:

Organic Chemistry Frontiers

The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition†

Fu-Sheng He,a   Cong-Shan Li,a   Hua Deng,a   Xing Zheng,a   Zhong-Tao Yanga  and  Wei-Ping Deng*a  

* Corresponding authors

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

Abstract

A highly efficient copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides with β-phthaliminoacrylate esters was developed under mild conditions, providing the desired pyrrolidine β-amino acid derivatives in high yields (up to 98%) with excellent diastereo- and enantioselectivities (dr >20 : 1, ee up to >99%). Subsequent deprotection and hydrogenolysis of the corresponding cycloadducts could deliver highly functionalized and biologically important free pyrrolidine β-amino acids in a straightforward and efficient pathway.

Graphical abstract: The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(i)-catalyzed asymmetric 1,3-dipolar cycloaddition

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Article information

DOI
https://doi.org/10.1039/C6QO00512H
Article type
Research Article
Submitted
05 Sep 2016
Accepted
07 Oct 2016
First published
08 Oct 2016

Org. Chem. Front., 2017,4, 52-56

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The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition

F. He, C. Li, H. Deng, X. Zheng, Z. Yang and W. Deng, Org. Chem. Front., 2017, 4, 52 DOI: 10.1039/C6QO00512H

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