Issue 1, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Catalytic asymmetric epoxidation of stilbene using a chiral salen complex immobilized in Mn-exchanged Al-MCM-41

Paola Piaggio,a   Christopher Langham,a   Paul McMorn,a   Donald Bethell,b   Philip C. Bulman-Page,c   Frederick E. Hancock,d   Chris Slye  and  Graham J. Hutchings*a  

* Corresponding authors

a Department of Chemistry, Cardiff University, PO Box 912, Cardiff, UK

b Department of Chemistry, University of Liverpool, Liverpool, UK

c Department of Chemistry, Loughborough University, Loughborough, Leicestershire, UK

d Synetix, R & T Division, PO Box 1, Billingham, Teeside, UK

e Robinson Brothers Ltd, Phoenix Street, West Bromwich, West Midlands, UK

Abstract

Manganese-exchanged Al-MCM-41 modified by the chiral salen ligand [(R,R)-(−)-N,N ′-bis(3,5-di-tert-butylsalicylidene)cyclohexane-1,2-diamine] can be used as an enantioselective heterogeneous epoxidation catalyst using iodosyl benzene as oxygen donor. Epoxidation of (Z )- and (E )-stilbene is studied in detail and experiments are described that demonstrate that the reaction is wholly catalysed heterogeneously. Similar enantioselectivity is observed for the oxidation of (Z )-stilbene to the (E )-epoxide using homogeneous (77.5% ee) or heterogeneous (70% ee) catalysts. The effect of temperature, solvents and donor ligands on the yield and enantioselection are discussed.

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Article information

DOI
https://doi.org/10.1039/A904900B
Article type
Paper
Submitted
21 Jun 1999
Accepted
01 Nov 1999
First published
24 Dec 1999

J. Chem. Soc., Perkin Trans. 2, 2000, 143-148

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Catalytic asymmetric epoxidation of stilbene using a chiral salen complex immobilized in Mn-exchanged Al-MCM-41

P. Piaggio, C. Langham, P. McMorn, D. Bethell, P. C. Bulman-Page, F. E. Hancock, C. Sly and G. J. Hutchings, J. Chem. Soc., Perkin Trans. 2, 2000, 143 DOI: 10.1039/A904900B

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