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

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dc.contributor.authorKissane, Marie
dc.contributor.authorLynch, Denis
dc.contributor.authorChopra, Jay
dc.contributor.authorLawrence, Simon E.
dc.contributor.authorMaguire, Anita R.
dc.contributor.funderIrish Research Council for Science Engineering and Technologyen
dc.contributor.funderEnterprise Irelanden
dc.contributor.funderBioResearch Irelanden
dc.contributor.funderForbairten
dc.contributor.funderUniversity College Corken
dc.date.accessioned2012-05-31T16:25:36Z
dc.date.available2012-05-31T16:25:36Z
dc.date.copyright2008
dc.date.issued2008-05-30
dc.description.abstractInvestigation 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.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKISSANE, 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.doi10.1016/j.tetasy.2008.04.033
dc.identifier.endpage1273en
dc.identifier.issn0957-4166
dc.identifier.issued10en
dc.identifier.journaltitleTetrahedron: Asymmetryen
dc.identifier.startpage1256en
dc.identifier.urihttps://hdl.handle.net/10468/599
dc.identifier.volume19en
dc.language.isoenen
dc.publisherElsevieren
dc.rightsNOTICE: 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.2008.04.033en
dc.subjectα-thio-β-chloroacrylamidesen
dc.subjectChemoselectiveen
dc.subjectEnantioselectiveen
dc.subjectKagan oxidationen
dc.subjectBolm oxidationen
dc.subject.lcshOxidationen
dc.subject.lcshOrganic compounds--Synthesisen
dc.titleInvestigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamidesen
dc.typeArticle (peer-reviewed)en
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