DOI10.1055s-0033-1339681.pdf (440.29 kB)
Activation of hydrogen peroxide by diphenyl diselenide for highly enantioselective oxaziridinium salt mediated catalytic asymmetric epoxidation
journal contribution
posted on 2014-01-10, 11:55 authored by Benjamin BuckleyBenjamin Buckley, Claire Elliott, Yohan Chan, Nicholas Dreyfus, Philip C. Bulman PageThe 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.
Funding
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.
History
School
- Science
Department
- Chemistry
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.Publisher
© Georg Thieme Verlag KGVersion
- AM (Accepted Manuscript)
Publication date
2013Notes
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-0033-1339681ISSN
0936-5214eISSN
1437-2096Publisher version
Language
- en