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Synlett 2008(9): 1381-1385
DOI: 10.1055/s-2008-1072592
DOI: 10.1055/s-2008-1072592
LETTER
© Georg Thieme Verlag Stuttgart · New York
Novel Binaphthalene-Amine Catalysts for the Asymmetric Epoxidation of Alkenes
Further Information
Received
27 February 2008
Publication Date:
16 April 2008 (online)
Publication History
Publication Date:
16 April 2008 (online)
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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