Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

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Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

Kissane, Marie; Lawrence, Simon E.; Maguire, Anita R.
Date: 2010-04-21
Copyright: Copyright © 2010 Elsevier Ltd. All rights reserved. NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Asymmetry. 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 Asymmetry, [VOL 21, ISSUE 7, (21/04/2010)] DOI 10.1016/j.tetasy.2010.05.004
Citation: KISSANE, M., LAWRENCE, S. E. & MAGUIRE, A. R. 2010. Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides. Tetrahedron: Asymmetry, 21, 871-884. doi: 10.1016/j.tetasy.2010.05.004
Published Version: 10.1016/j.tetasy.2010.05.004

Abstract:

Diastereoselective sulfur oxidation in 2-thio-3-chloroacrylamides is described. A range of chiral amine auxiliaries were incorporated in the β-chloroacrylamide, and the efficiency with which the stereochemistry was relayed to the sulfur centre during sulfoxidation was investigated. Diastereomeric ratios of up to 3.3:1 were achieved.

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