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Highly diastereoselective synthesis of cyclopropane-fused spiro-pseudoindoxyl derivatives through [2 + 1] annulation of 2-ylideneoxindoles and sulfonium bromides

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Abstract

Compared with the intensively studied C3 spirooxindoles, limited reliable approaches are reported for synthesizing structurally analogous C2-spiropseudoindoxyl derivatives. Here, we developed an efficient method for highly diastereoselective synthesis of cyclopropane-fused spiropseudoindoxyl derivatives (up to 88% yield and >20 : 1 dr in all cases) through [2 + 1] annulation of (Z)-2-ylideneoxindoles with sulfur ylides.

Graphical abstract: Highly diastereoselective synthesis of cyclopropane-fused spiro-pseudoindoxyl derivatives through [2 + 1] annulation of 2-ylideneoxindoles and sulfonium bromides

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Publication details

The article was received on 20 Aug 2018, accepted on 12 Oct 2018 and first published on 12 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02034E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Highly diastereoselective synthesis of cyclopropane-fused spiro-pseudoindoxyl derivatives through [2 + 1] annulation of 2-ylideneoxindoles and sulfonium bromides

    X. Tang, H. Zhu, J. Zhou, Y. Chen, X. Pan, L. Guo, J. Li, C. Peng and W. Huang, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02034E

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