Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

cbnd
Thumbnail Image
Files
Date
2010-04-21
Authors
Kissane, Marie
Lawrence, Simon E.
Maguire, Anita R.
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Published Version
10.1016/j.tetasy.2010.05.004
Research Projects
Organizational Units
Journal Issue
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.
Description
Keywords
Diastereoselective oxidation , Sulfur oxidation , 2-thio-3-chloroacrylamides , Chiral amine auxiliaries , beta-chloroacrylamide , Sulfoxidation , Diastereomeric ratios
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
Link to publisher’s version
URI
https://hdl.handle.net/10468/587
Collections
Chemistry - Journal Articles
Analytical & Biological Chemistry Research Facility - Journal Articles
Pharmacy - Journal Articles
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