Novel binaphthalene-amine catalysts for the asymmetric epoxidation of alkenes

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

doi:10.1055/s-2008-1072592

Novel binaphthalene-amine catalysts for the asymmetric epoxidation of alkenes

Philip Bulman Page, Mohamed Farah, Benjamin Buckley, A. John Blacker, Jérôme Lacour

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1381-1385
Number of pages	5
Journal	Synlett
Volume	2008
Issue number	9
DOIs	https://doi.org/10.1055/s-2008-1072592
Publication status	Published - 2008

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10.1055/s-2008-1072592

Cite this

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title = "Novel binaphthalene-amine catalysts for the asymmetric epoxidation of alkenes",

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.",

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AU - Farah, Mohamed

AU - Buckley, Benjamin

AU - Blacker, A. John

AU - Lacour, Jérôme

PY - 2008

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AB - 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.

U2 - 10.1055/s-2008-1072592

DO - 10.1055/s-2008-1072592

M3 - Article

VL - 2008

SP - 1381

EP - 1385

JO - Synlett

JF - Synlett

SN - 0936-5214

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