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Issue 1, 2017
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The facile and stereoselective synthesis of pyrrolidine β-amino acids via copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition

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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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Publication details

The article was received on 05 Sep 2016, accepted on 07 Oct 2016 and first published on 08 Oct 2016


Article type: Research Article
DOI: 10.1039/C6QO00512H
Citation: 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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