Novel Binaphthalene-Amine Catalysts for the Asymmetric Epoxidation of Alkenes

Philip C. Bulman Page; Mohamed M. Farah; Benjamin R. Buckley; A. John Blacker; Jérôme Lacour

doi:10.1055/s-2008-1072592

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Synlett 2008(9): 1381-1385
DOI: 10.1055/s-2008-1072592

LETTER

Novel Binaphthalene-Amine Catalysts for the Asymmetric Epoxidation of Alkenes

Philip C. Bulman Page*^a, Mohamed M. Farah^b, Benjamin R. Buckley^b, A. John Blacker^c, Jérôme Lacour^d
^a School of Chemical Sciences & Pharmacy, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK
Fax: +44(1603)592003; e-Mail: p.page@uea.ac.uk;
^b Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK
^c NPIL Pharmaceuticals (UK) Ltd, P.O. Box 521, Leeds Road, Huddersfield HD2 1GA, UK
^d Department of Chemistry, University of Geneva, 1211 Geneva 4, Switzerland

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Publication History

Received 27 February 2008
Publication Date:
16 April 2008 (online)

Abstract
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Abstract

We have prepared a range of binaphthalene-derived azepine derivatives containing alcohol functionality, and used them as catalysts in the asymmetric epoxidation of alkenes by Oxone, giving ee values of up to 81%. We have obtained evidence that points to the involvement of iminium ions in the reaction pathway, suggesting that the oxidizing species in the epoxidation reactions are in fact the corresponding oxaziridinium ions.

Key words

asymmetric - Oxone - epoxidation - alkene - epoxide

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