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Issue 19, 2014
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Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: a reliable access to enantioenriched pyrrolidin-3-ones

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Abstract

A gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides has been developed, which provides a reliable access to synthetically useful chiral pyrrolidin-3-ones with excellent ee, by combining the chiral tert-butylsulfinimine chemistry and gold catalysis. This methodology has also been used in the facile synthesis of natural product (−)-irniine. The use of readily available starting materials, a broad substrate scope, a simple procedure and the mild nature of this reaction render it a viable alternative for the synthesis of enantioenriched pyrrolidin-3-ones.

Graphical abstract: Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: a reliable access to enantioenriched pyrrolidin-3-ones

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Publication details

The article was received on 05 Dec 2013, accepted on 04 Jan 2014 and first published on 07 Jan 2014


Article type: Communication
DOI: 10.1039/C3CC49238A
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 2522-2525
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    Gold-catalyzed intermolecular oxidation of chiral homopropargyl sulfonamides: a reliable access to enantioenriched pyrrolidin-3-ones

    C. Shu, L. Li, Y. Yu, S. Jiang and L. Ye, Chem. Commun., 2014, 50, 2522
    DOI: 10.1039/C3CC49238A

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