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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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Supplementary files

Article information


Submitted
20 Nov 2018
Accepted
04 Jan 2019
First published
04 Jan 2019

Chem. Commun., 2019,55, 1398-1401
Article type
Communication

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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