Synthesis and stereoselective oxidation of α-Thio-β- chloropropenyloxazolidin-2-ones

Show simple item record Kissane, Marie Murphy, Maureen Lawrence, Simon E. Maguire, Anita R. 2012-05-09T16:01:25Z 2012-05-09T16:01:25Z 2010 2010-11-08
dc.identifier.citation KISSANE, M., MURPHY, M., LAWRENCE, S. E. & MAGUIRE, A. R. 2010. Synthesis and stereoselective oxidation of α-thio-β-chloropropenyloxazolidin-2-ones. Tetrahedron: Asymmetry, 21, 2550-2558. doi: 10.1016/j.tetasy.2010.10.007 en
dc.identifier.volume 21 en
dc.identifier.issued 20 en
dc.identifier.startpage 2550 en
dc.identifier.endpage 2558 en
dc.identifier.issn 0957-4166
dc.identifier.doi 10.1016/j.tetasy.2010.10.007
dc.description.abstract Investigation of the stereoselective reaction of α-thiopropanoyloxazolidin-2-ones with NCS to yield α-thio-β-chloropropenyloxazolidin-2-ones is described. Diastereoselective sulfur oxidation of the resulting α-thio-β-chloropropenyloxazolidin-2-ones is also discussed, with modest diastereocontrol achieved. However, through a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation, diastereoselectivities of up to 94% de are achieved. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher Elsevier en
dc.rights © 2010 Elsevier Ltd. 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, [21, 20, (08/11/2010)] DOI: 10.1016/j.tetasy.2010.10.007 en
dc.subject Stereoselective en
dc.subject α-thiopropanoyloxazolidin-2-ones en
dc.subject α-thio-β-chloropropenyloxazolidin-2-ones en
dc.subject Diastereoselectivities en
dc.subject NCS en
dc.subject.lcsh Oxidation en
dc.subject.lcsh Stereochemistry en
dc.title Synthesis and stereoselective oxidation of α-Thio-β- chloropropenyloxazolidin-2-ones en
dc.type Article (peer-reviewed) en
dc.internal.authorurl en
dc.internal.authorcontactother Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry, University Colllege Cork, Ireland. T:+353 21 4901693 E: en
dc.internal.availability Full text available en
dc.description.version Accepted Version en
dc.internal.rssid 70046411 en
dc.contributor.funder Irish Research Council for Science Engineering and Technology en
dc.contributor.funder University College Cork en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Tetrahedron: Asymmetry en
dc.internal.copyrightchecked Checked Sherpa Romeo. Consulted publisher website: en
dc.internal.IRISemailaddress en
dc.internal.IRISemailaddress en

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