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Issue 44, 2015
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The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

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Abstract

A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97% ee).

Graphical abstract: The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

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The article was received on 20 Mar 2015, accepted on 28 Apr 2015 and first published on 28 Apr 2015


Article type: Communication
DOI: 10.1039/C5CC02362A
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Citation: Chem. Commun., 2015,51, 9212-9215
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    The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

    W. Yang, Y. Liu, S. Luo, X. Yu, J. S. Fossey and W. Deng, Chem. Commun., 2015, 51, 9212
    DOI: 10.1039/C5CC02362A

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