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Issue 7, 2016
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Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar cycloaddition reaction of azlactones

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Abstract

The first chiral phosphoric acid catalyzed highly diastereo- and enantioselective 1,3-dipolar cycloaddition reaction of azlactones and methyleneindolinones was disclosed. By using a BINOL-derived chiral phosphoric acid as the catalyst, azlactones were activated as chiral anti N-protonated 1,3-dipoles to react with methyleneindolinones to yield biologically important 3,3′-pyrrolidonyl spirooxindole scaffolds in high yields, with good-to-excellent diastereo- and enantioselectivity.

Graphical abstract: Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar cycloaddition reaction of azlactones

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Publication details

The article was received on 29 Oct 2015, accepted on 24 Nov 2015 and first published on 24 Nov 2015


Article type: Communication
DOI: 10.1039/C5CC08989A
Citation: Chem. Commun., 2016,52, 1377-1380

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    Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar cycloaddition reaction of azlactones

    Z. Zhang, W. Sun, G. Zhu, J. Yang, M. Zhang, L. Hong and R. Wang, Chem. Commun., 2016, 52, 1377
    DOI: 10.1039/C5CC08989A

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