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Issue 42, 2012
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Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones

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Abstract

A stereoselective [3+2] cycloaddition of isocyanoesters to methyleneindolinones catalyzed by a quinine-based thiourea-tertiary amine has been successfully developed. Just by tuning the protecting groups on substrates, a variety of optically enriched 3,3′-pyrrolidinyl spirooxindole diastereomers could be obtained in excellent enantioselectivities (up to 99% ee).

Graphical abstract: Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones

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Publication details

The article was received on 02 Feb 2012, accepted on 30 Mar 2012 and first published on 02 Apr 2012


Article type: Communication
DOI: 10.1039/C2CC30746D
Citation: Chem. Commun., 2012,48, 5175-5177
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    Organocatalytic stereocontrolled synthesis of 3,3′-pyrrolidinyl spirooxindoles by [3+2] annulation of isocyanoesters with methyleneindolinones

    L. Wang, J. Bai, L. Peng, L. Qi, L. Jia, Y. Guo, X. Luo, X. Xu and L. Wang, Chem. Commun., 2012, 48, 5175
    DOI: 10.1039/C2CC30746D

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