Issue 19, 2014

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

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Dec 2013
Accepted
04 Jan 2014
First published
07 Jan 2014

Chem. Commun., 2014,50, 2522-2525

Author version available

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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