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Synlett 2013; 24(17): 2266-2270
DOI: 10.1055/s-0033-1339681
letter
© Georg Thieme Verlag Stuttgart · New York

Activation of Hydrogen Peroxide by Diphenyl Diselenide for Highly Enantioselective Oxaziridinium Salt Mediated Catalytic Asymmetric Epoxidation

Benjamin R. Buckley*
a   Department of Chemistry, Loughborough University, Ashby Road, Loughborough, Leicestershire, LE11 3TU, UK   Fax: +44(1509)223925   eMail: b.r.buckley@lboro.ac.uk
,
Claire E. Elliott
a   Department of Chemistry, Loughborough University, Ashby Road, Loughborough, Leicestershire, LE11 3TU, UK   Fax: +44(1509)223925   eMail: b.r.buckley@lboro.ac.uk
,
Yohan Chan
b   School of Chemistry, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK   eMail: p.page@uea.ac.uk
,
Nicholas Dreyfus
c   Eli Lilly, Erl Wood Manor, Erl Wood, Windlesham, Surrey, UK
,
Philip C. Bulman Page*
b   School of Chemistry, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK   eMail: p.page@uea.ac.uk
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Publikationsverlauf

Received: 14. Juli 2013

Accepted after revision: 07. August 2013

Publikationsdatum:
10. September 2013 (online)

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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.

Key words

epoxidation - iminium salt - oxaziridinium - diphenyl diselenide - oxidation
 

  • References and Notes

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