Issue 10, 2011
From the journal:

Organic & Biomolecular Chemistry

Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds†

Julia A. Griffen,a   Amélie M. Le Coz,b   Gabriele Kociok-Köhn,a   Monika Ali Khan,a   Alan J. W. Stewartc  and  Simon E. Lewis*a  

* Corresponding authors

a Doctoral Training Centre in Sustainable Chemical Technologies, University of Bath, Bath, UK
E-mail: S.E.Lewis@bath.ac.uk
Fax: +44 (0)1225 386231
Tel: +44 (0)1225 386568

b ESCOM, 1 Allée du Réseau Jean-Marie Buckmaster, Compiègne, France

c Prosidion Limited, Windrush Court, Watlington Road, Oxford, UK

Abstract

Metabolism of meta-bromobenzoic acid by the blocked mutant Ralstonia eutrophus B9 affords an enantiopure dearomatised halodiene-diol which we demonstrate is a versatile chiron for organic synthesis. The presence of the halogen leads to reactivity that is distinct to that observed for the non-halogenated analogue and also serves as a synthetic handle for further functionalisation.

Graphical abstract: Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds

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Article information

DOI
https://doi.org/10.1039/C1OB05131H
Article type
Paper
Submitted
24 Jan 2011
Accepted
07 Mar 2011
First published
06 Apr 2011

Org. Biomol. Chem., 2011,9, 3920-3928

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Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds

J. A. Griffen, A. M. Le Coz, G. Kociok-Köhn, M. A. Khan, A. J. W. Stewart and S. E. Lewis, Org. Biomol. Chem., 2011, 9, 3920 DOI: 10.1039/C1OB05131H

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