103. 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
     Synlett 2008, 1381-1385

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.

DOI : 10.1055/s-2008-1072592 

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