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The one pot asymmetric synthesis of 3,3′-pyrrolidonyl spiroxindoles via a regio- and stereoselective domino reaction

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Abstract

A highly efficient regio- and stereoselective domino aziridine ring opening and lactamization reaction between aziridines and 3-carboxy oxindole esters has been developed for the one pot asymmetric synthesis of 4-aryl-3,3′-spiropyrrolidonyl oxindoles with excellent selectivity (dr >99 : 1 and ee up to >99%). It was further extended to a sequential one pot protocol for the asymmetric synthesis of NH-free 3,3′-pyrrolidonyl spiroxindole, maintaining the same selectivity.

Graphical abstract: The one pot asymmetric synthesis of 3,3′-pyrrolidonyl spiroxindoles via a regio- and stereoselective domino reaction

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Publication details

The article was received on 15 Jul 2019, accepted on 06 Aug 2019 and first published on 07 Aug 2019


Article type: Paper
DOI: 10.1039/C9OB01570A
Org. Biomol. Chem., 2019, Advance Article

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    The one pot asymmetric synthesis of 3,3′-pyrrolidonyl spiroxindoles via a regio- and stereoselective domino reaction

    S. Hajra, S. S. Bhosale, A. Hazra and N. Kanaujia, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01570A

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