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

dc.contributor.authorKissane, Marie
dc.contributor.authorMurphy, Maureen
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.accessioned2012-05-09T16:01:25Z
dc.date.available2012-05-09T16:01:25Z
dc.date.copyright2010
dc.date.issued2010-11-08
dc.description.abstractInvestigation 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.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKISSANE, 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.2010.10.007en
dc.identifier.doi10.1016/j.tetasy.2010.10.007
dc.identifier.endpage2558en
dc.identifier.issn0957-4166
dc.identifier.issued20en
dc.identifier.journaltitleTetrahedron: Asymmetryen
dc.identifier.startpage2550en
dc.identifier.urihttps://hdl.handle.net/10468/577
dc.identifier.volume21en
dc.language.isoenen
dc.publisherElsevieren
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.2010.10.007en
dc.subjectStereoselectiveen
dc.subjectα-thiopropanoyloxazolidin-2-onesen
dc.subjectα-thio-β-chloropropenyloxazolidin-2-onesen
dc.subjectDiastereoselectivitiesen
dc.subjectNCSen
dc.subject.lcshOxidationen
dc.subject.lcshStereochemistryen
dc.titleSynthesis and stereoselective oxidation of α-Thio-β- chloropropenyloxazolidin-2-onesen
dc.typeArticle (peer-reviewed)en
Files
Original bundle
Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
MK_SynthesisAV2010.pdf
Size:
732.44 KB
Format:
Adobe Portable Document Format
Description:
Accepted Version
License bundle
Now showing 1 - 1 of 1
Loading...
Thumbnail Image
Name:
license.txt
Size:
4.04 KB
Format:
Item-specific license agreed upon to submission
Description: