Issue 12, 2003
From the journal:

Organic & Biomolecular Chemistry

Scope of the directed dihydroxylation: application to cyclic homoallylic alcohols and trihaloacetamides

Timothy J. Donohoe,*a   Lee Mitchell,b   Michael J. Waring,b   Madeleine Helliwell,†b   Andrew Bellc  and  Nicholas J. Newcombed  

* Corresponding authors

a Dyson Perrins Laboratory, South Parks Road, Oxford, UK

b Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK

c Pfizer Global Research and Development, Sandwich, Kent, UK

d AstraZeneca Pharmaceuticals, Mereside, Alderley Park, Macclesfield, Cheshire, UK

Abstract

The synthesis and directed dihydroxylation of a range of cyclic alkenes was investigated. Both homoallylic alcohols and homoallylic trihaloacetamides were found to be efficient directing groups, giving rise to good to excellent levels of remote asymmetric induction with OsO4–TMEDA. Interestingly, in all cases examined, trifluoroacetamides were found to be superior to trichloroacetamides as directing groups and an argument is presented which rationalises this observation.

Graphical abstract: Scope of the directed dihydroxylation: application to cyclic homoallylic alcohols and trihaloacetamides

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Article information

DOI
https://doi.org/10.1039/B303081D
Article type
Paper
Submitted
20 Mar 2003
Accepted
12 May 2003
First published
27 May 2003

Org. Biomol. Chem., 2003,1, 2173-2186

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Scope of the directed dihydroxylation: application to cyclic homoallylic alcohols and trihaloacetamides

T. J. Donohoe, L. Mitchell, M. J. Waring, M. Helliwell, A. Bell and N. J. Newcombe, Org. Biomol. Chem., 2003, 1, 2173 DOI: 10.1039/B303081D

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