Selective β-oxidation of α-sulfanyl amides

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Selective β-oxidation of α-sulfanyl amides

Kissane, Marie; Murphy, Maureen; Bateman, Lorraine M.; McCarthy, Daniel G.; Maguire, Anita R.
Date: 2011-07-29
Copyright: Copyright © 2011 Elsevier Ltd. All rights reserved. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron, [67, 30, (14/05/2011)] DOI 10.1016/j.tet.2011.05.041
Citation: KISSANE, M., MURPHY, M., BATEMAN, L. M., MCCARTHY, D. G. & MAGUIRE, A. R. 2011. Selective β-oxidation of α-sulfanyl amides. Tetrahedron, 67, 5494-5499. doi: 10.1016/j.tet.2011.05.041
Published Version: 10.1016/j.tet.2011.05.041

Abstract:

A selective β-oxidation of a series of α-sulfanyl amides to the corresponding β-oxo-α-sulfanyl amides is described. This selective efficient oxidation of an unfunctionalised methyl or methylene group occurs under mild conditions, involving three sequential transformations conducted without isolation of the intermediates. Critically neither the sulfur nor the reactive α-CH bond is affected in the overall process.

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