Issue 11, 2007
From the journal:

Organic & Biomolecular Chemistry

Epoxidation–alcoholysis of cyclic enol ethers catalyzed by Ti(OiPr)4 or Venturello's peroxophosphotungstate complex

Pieter Levecque,ab   David Gammon,b   Henok Hadgu Kinfe,†b   Pierre Jacobs,a   Dirk De Vosa  and  Bert Sels*a  

* Corresponding authors

a Centre for Surface Chemistry and Catalysis, K.U.Leuven, Kasteelpark Arenberg 23, Heverlee, Belgium
E-mail: Bert.Sels@biw.kuleuven.be
Fax: (+32)16 321998

b Department of Chemistry, University of Cape Town, Private Bag, Rondebosch, South Africa

Abstract

Venturello's peroxophosphotungstate compound and Ti(OiPr)4 were successfully used as catalysts for the epoxidation–alcoholysis of various dihydropyrans and dihydrofuran using H2O2 as the oxidant. Different alcohols can be used as solvents and nucleophiles, resulting in hydroxy ether products with varying alkoxy groups. The Venturello compound can also be used as catalyst in a biphasic conversion of dihydropyran, in which long chain alcohols or fatty acids are incorporated in the hydroxy ether products with high yield and (stereo)selectivity.

Graphical abstract: Epoxidation–alcoholysis of cyclic enol ethers catalyzed by Ti(OiPr)4 or Venturello's peroxophosphotungstate complex

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Article information

DOI
https://doi.org/10.1039/B705244H
Article type
Paper
Submitted
10 Apr 2007
Accepted
18 Apr 2007
First published
08 May 2007

Org. Biomol. Chem., 2007,5, 1800-1806

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Epoxidation–alcoholysis of cyclic enol ethers catalyzed by Ti(OiPr)4 or Venturello's peroxophosphotungstate complex

P. Levecque, D. Gammon, H. H. Kinfe, P. Jacobs, D. De Vos and B. Sels, Org. Biomol. Chem., 2007, 5, 1800 DOI: 10.1039/B705244H

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