Diastereoselective sulfur oxidation of 2-thio-3-chloroacrylamides

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dc.contributor.authorKissane, Marie
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderUniversity College Corken
dc.date.accessioned2012-05-14T16:00:39Z
dc.date.available2012-05-14T16:00:39Z
dc.date.copyright2010-04-21
dc.date.issued2010-04-21
dc.description.abstractDiastereoselective 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.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKISSANE, 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.2010.05.004en
dc.identifier.doi10.1016/j.tetasy.2010.05.004
dc.identifier.endpage884en
dc.identifier.issn0957-4166
dc.identifier.issn1362-511X
dc.identifier.issued7en
dc.identifier.journaltitleTetrahedron Asymmetryen
dc.identifier.startpage871en
dc.identifier.urihttps://hdl.handle.net/10468/587
dc.identifier.volume21en
dc.language.isoenen
dc.publisherElsevieren
dc.rights© 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.2010.05.004en
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectDiastereoselective oxidationen
dc.subjectSulfur oxidationen
dc.subject2-thio-3-chloroacrylamidesen
dc.subjectChiral amine auxiliariesen
dc.subjectbeta-chloroacrylamideen
dc.subjectSulfoxidationen
dc.subjectDiastereomeric ratiosen
dc.subject.lcshStereochemistryen
dc.titleDiastereoselective sulfur oxidation of 2-thio-3-chloroacrylamidesen
dc.typeArticle (peer-reviewed)en
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