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Title: Activation of hydrogen peroxide by diphenyl diselenide for highly enantioselective oxaziridinium salt mediated catalytic asymmetric epoxidation
Authors: Buckley, Benjamin R.
Elliott, Claire
Chan, Yohan
Dreyfus, Nicholas
Page, Philip C. Bulman
Keywords: Epoxidation
Iminium salt
Oxaziridinium
Diphenyl diselenide
Oxidation
Issue Date: 2013
Publisher: © Georg Thieme Verlag KG
Citation: BUCKLEY, B.R. ... et al., 2013. Activation of hydrogen peroxide by diphenyl diselenide for highly enantioselective oxaziridinium salt mediated catalytic asymmetric epoxidation. Synlett, 24 (17), pp. 2266-2270.
Abstract: The first reported use of benzeneperseleninic acid as a catalytic mediator for oxaziridinium ion catalysed epoxidation is described, providing reaction rates and ee values (up to 85%) similar to those reported when using oxone as the stoichiometric oxidant. A dual catalytic cycle is proposed, in which diphenyl diselenide is initially converted into the perseleninic acid, which in turn oxidises an iminium ion to the corresponding oxaziridinium species, thus facilitating asymmetric oxygen transfer to an alkene. © Georg Thieme Verlag.
Description: This article was published as a letter in the journal, Synlett [© Georg Thieme Verlag] and the definitive version is available at: http://dx.doi.org/10.1055/s-0033-1339681
Sponsor: Eli Lilly. EPSRC (CASE award to C.E.), Loughborough University and the University of East Anglia. The Royal Society for an Industry Fellowship (to P.C.B.P.), Research Councils UK for a RCUK Fellowship (to B.R.B.), and the EPSRC National Mass Spectrometry Facility, Swansea.
Version: Accepted for publication
DOI: 10.1055/s-0033-1339681
URI: https://dspace.lboro.ac.uk/2134/13944
Publisher Link: http://dx.doi.org/10.1055/s-0033-1339681
ISSN: 0936-5214
Appears in Collections:Published Articles (Chemistry)

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