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Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

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Abstract

A highly efficient method for the enantioselective construction of dispirocyclic compounds has been developed by the squaramide-catalysed asymmetric Michael addition/cyclization cascade reaction of 2,3-dioxopyrrolidines with 3-chlorooxindoles. The corresponding chiral dispiro[indoline-3,1′-cyclopropane-2′,3′′-pyrrolidine]-2,4′′,5′′-triones were obtained in high yields with excellent stereoselectivities (up to 94% yield, >25 : 1 dr and >99% ee). Furthermore, a gram-scale experiment confirmed the reliability of the current reaction and further effective transformation of the product has been realized.

Graphical abstract: Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

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Article information


Submitted
14 Dec 2019
Accepted
03 Feb 2020
First published
04 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Squaramide-catalysed asymmetric cascade reactions of 2,3-dioxopyrrolidines with 3-chlorooxindoles

J. Wen and D. Du, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02663K

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