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Issue 10, 2019
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A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

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Abstract

An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates the usefulness of the latter as efficient Michael acceptors in generating complex caged products in 26–92% yields, 14–98% ee and up to >25 : 1 d.r. values.

Graphical abstract: A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

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Publication details

The article was received on 20 Nov 2018, accepted on 04 Jan 2019 and first published on 04 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC09219B
Citation: Chem. Commun., 2019,55, 1398-1401

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    A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters

    S. Yang, P. Karanam, M. Wang, Y. Jang, Y. Yeh, P. Tseng, M. R. Ganapuram, Y. Liou and W. Lin, Chem. Commun., 2019, 55, 1398
    DOI: 10.1039/C8CC09219B

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