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

Piaggio, Paola, Langham, Christopher, McMorn, Paul, Bethell, Donald, Bulman Page, Philip C., Hancock, Frederick E., Sly, Chris and Hutchings, Graham J. (2000) Catalytic asymmetric epoxidation of stilbene using a chiral salen complex immobilized in Mn-exchanged Al-MCM-41. Journal of the Chemical Society-Perkin Transactions 2, 1. pp. 143-148. ISSN 0300-9580

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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-diamin e] 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.

Item Type: Article
Uncontrolled Keywords: design,hydrogenation,mcm-41,enantioselective epoxidation,unfunctionalized olefins,oxidations
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 11:49
Last Modified: 21 Apr 2020 21:18
URI: https://ueaeprints.uea.ac.uk/id/eprint/32815
DOI: 10.1039/A904900B

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