Copper-catalyzed asymmetric oxidation of sulfides

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dc.contributor.author O'Mahony, Graham E.
dc.contributor.author Ford, Alan
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2013-02-26T09:57:54Z
dc.date.available 2013-02-26T09:57:54Z
dc.date.issued 2012-02-24
dc.identifier.citation O’MAHONY, G. E., FORD, A. & MAGUIRE, A. R. 2012. Copper-Catalyzed Asymmetric Oxidation of Sulfides. Journal of organic chemistry, 77 (7), 3288-3296. doi: 10.1021/jo2026178 en
dc.identifier.volume 77 en
dc.identifier.issued 7 en
dc.identifier.startpage 3288 en
dc.identifier.endpage 3296 en
dc.identifier.uri http://hdl.handle.net/10468/988
dc.identifier.doi 10.1021/jo2026178
dc.description.abstract Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee). en
dc.description.sponsorship IRCSET (EMBARK Initiative) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher ACS Publications en
dc.relation.uri http://pubs.acs.org/doi/abs/10.1021/jo2026178
dc.rights © 2011, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher.To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jo2026178 en
dc.subject Copper-catalyzed en
dc.subject Asymmetric en
dc.subject Oxidation en
dc.subject Sulfides en
dc.subject Sulfoxidation en
dc.title Copper-catalyzed asymmetric oxidation of sulfides en
dc.type Article (peer-reviewed) en
dc.internal.authorurl http://publish.ucc.ie/researchprofiles/V001/amaguire en
dc.internal.authorcontactother Anita Maguire, Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Ireland. T.:+353 (0)21 4901694 E-mail: a.maguire@ucc.ie en
dc.internal.availability Full text available en
dc.description.version Accepted Version en
dc.contributor.funder Irish Research Council for Science Engineering and Technology en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Journal of Organic Chemistry en
dc.internal.IRISemailaddress a.maguire@ucc.ie en


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