Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds†
Julia A. Griffen,Amélie M. Le Coz,Gabriele Kociok-Köhn,Monika Ali Khan,Alan J. W. Stewart,Simon E. Lewis
Organic & Biomolecular Chemistry Pub Date : 04/06/2011 00:00:00 , DOI:10.1039/C1OB05131H
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