Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides

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dc.contributor.author Kissane, Marie
dc.contributor.author Lynch, Denis
dc.contributor.author Chopra, Jay
dc.contributor.author Lawrence, Simon E.
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2012-05-31T16:25:36Z
dc.date.available 2012-05-31T16:25:36Z
dc.date.copyright 2008
dc.date.issued 2008-05-30
dc.identifier.citation KISSANE, M., LYNCH, D., CHOPRA, J., LAWRENCE, S. E. & MAGUIRE, A. R. 2008. Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides. Tetrahedron: Asymmetry, 19, 1256-1273. en
dc.identifier.volume 19 en
dc.identifier.issued 10 en
dc.identifier.startpage 1256 en
dc.identifier.endpage 1273 en
dc.identifier.issn 0957-4166
dc.identifier.uri http://hdl.handle.net/10468/599
dc.identifier.doi 10.1016/j.tetasy.2008.04.033
dc.description.abstract Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides is described. The α-thio-β-chloroacrylamides can be selectively oxidized to either the racemic sulfoxide or the sulfone very efficiently. The asymmetric sulfur oxidation of α-thio-β-chloroacrylamides is also discussed, with sulfoxide enantioselectivites of up to 52% ee achieved using the Kagan oxidation, and up to 71% ee when the Bolm oxidation is employed. While the enantioselectivities achieved are modest, these are among the most highly functionalised sulfides investigated in catalytic asymmetric oxidation, and the resulting enantioenriched sulfoxides have significant synthetic potential. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Elsevier en
dc.rights 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 Tetrhedron Asymmetry, [19, 10, (30/05/2008)] 10.1016/j.tetasy.2008.04.033 en
dc.subject α-thio-β-chloroacrylamides en
dc.subject Chemoselective en
dc.subject Enantioselective en
dc.subject Kagan oxidation en
dc.subject Bolm oxidation en
dc.subject.lcsh Oxidation en
dc.subject.lcsh Organic compounds--Synthesis en
dc.title Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides en
dc.type Article (peer-reviewed) en
dc.internal.authorurl http://publish.ucc.ie/researchprofiles/V001/amaguire en
dc.internal.authorcontactother Department of Chemistry & School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland. Tel. no.: +353 (0)21 4901694 en
dc.internal.availability Full text available en
dc.description.version Accepted Version en
dc.internal.rssid 723558 en
dc.contributor.funder Irish Research Council for Science Engineering and Technology en
dc.contributor.funder Enterprise Ireland en
dc.contributor.funder BioResearch Ireland en
dc.contributor.funder Forbairt en
dc.contributor.funder University College Cork en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Tetrahedron: Asymmetry en
dc.internal.copyrightchecked Checked Elsevier website: http://www.elsevier.com/wps/find/authorsview.authors/postingpolicy Added text as required by publishers: http://www.elsevier.com/wps/find/authorsview.authors/postingpolicy en
dc.internal.IRISemailaddress a.maguire@ucc.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en
dc.internal.IRISemailaddress denis.lynch@ucc.ie en


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