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Issue 21, 2008
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Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

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Abstract

cis-Dihydrodiol metabolites were obtained from dioxygenase-catalysed asymmetric dihydroxylations of five monocyclic (azabiphenyl) and four tricyclic (azaphenanthrene) azaarene substrates. Enantiopurity values and absolute configuration assignments were determined using a combination of stereochemical correlation, X-ray crystallography and spectroscopy methods. The degree of regioselectivity found during cis-dihydroxylation of monocyclic azaarenes (2,3 bond >> 3,4 bond) and of tricyclic azaarenes (bay region > non-bay region bonds) was dependent on the type of dioxygenase used. The cis-dihydrodiol metabolite from an azaarene (3-phenylpyridine) was utilised in the chemoenzymatic synthesis of the corresponding trans-dihydrodiol.

Graphical abstract: Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

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Article information


Submitted
17 Jun 2008
Accepted
29 Jul 2008
First published
05 Sep 2008

Org. Biomol. Chem., 2008,6, 3957-3966
Article type
Paper

Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates

D. R. Boyd, N. D. Sharma, G. P. Coen, F. Hempenstall, V. Ljubez, J. F. Malone, C. C. R. Allen and J. T. G. Hamilton, Org. Biomol. Chem., 2008, 6, 3957
DOI: 10.1039/B810235J

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