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

Julia A Griffen; A M Le Coz; Gabriele Kociok-Kohn; Monika Ali Khan; A J W Stewart; Simon E Lewis

doi:10.1039/c1ob05131h

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

Julia A Griffen, A M Le Coz, Gabriele Kociok-Kohn, Monika Ali Khan, A J W Stewart, Simon E Lewis

Department of Chemistry

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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.

Original language	English
Pages (from-to)	3920-3928
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	10
DOIs	https://doi.org/10.1039/c1ob05131h
Publication status	Published - 21 May 2011

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AU - Griffen, Julia A

AU - Le Coz, A M

AU - Kociok-Kohn, Gabriele

AU - Ali Khan, Monika

AU - Stewart, A J W

AU - Lewis, Simon E

PY - 2011/5/21

Y1 - 2011/5/21

N2 - 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.

AB - 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.

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UR - http://dx.doi.org/10.1039/c1ob05131h

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DO - 10.1039/c1ob05131h

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IS - 10

ER -

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

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