Issue 26, 2021

Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with o-quinones

Abstract

Spirocyclic o-quinone analogues show a broad spectrum of applications as biologically active compounds. We herein report the chiral bifunctional squaramide catalysed asymmetric vinylogous aldol-cyclization cascade reaction between 3-alkylidene oxindoles and o-quinones. A wide range of enantioenriched spirocyclic o-quinone analogues with a quaternary stereocenter could be smoothly synthesized in good to excellent yields (up to 99%) with high enantioselectivities (up to 99%).

Graphical abstract: Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with o-quinones

Supplementary files

Article information

Article type
Paper
Submitted
06 May 2021
Accepted
01 Jun 2021
First published
02 Jun 2021

Org. Biomol. Chem., 2021,19, 5836-5843

Enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with o-quinones

Y. Tsou, R. Guan and J. Han, Org. Biomol. Chem., 2021, 19, 5836 DOI: 10.1039/D1OB00888A

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