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Valuable new cyclohexadiene building blocks from cationic η5-iron-carbonyl complexes derived from a microbial arene oxidation product


Reference:

Ali Khan, M., Mahon, M. F., Lowe, J. P., Stewart, A. J. W. and Lewis, S. E., 2012. Valuable new cyclohexadiene building blocks from cationic η5-iron-carbonyl complexes derived from a microbial arene oxidation product. Chemistry - A European Journal, 18 (42), pp. 13480-13493.

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Official URL:

http://dx.doi.org/10.1002/chem.201202411

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Abstract

Biooxidation of benzoic acid by Ralstonia eutropha B9 provides an unusual cyclohexadiene carboxy diol that contains a quaternary stereocentre. Tricarbonyliron derivatives of this chiron, on treatment with acid, give two isomeric η5-cyclohexadienyl complexes as observed by NMR spectroscopy. Both of these can be subjected to the addition of nucleophiles to provide isomeric cyclohexadiene complexes with new substituent patterns, several of which have been characterised crystallographically. De-metallation of these provides a versatile library of cyclohexadiene building blocks, the utility of which is demonstrated by formal syntheses of oseltamivir. The mechanism of product formation and its stereochemical implications are discussed, as are the procedures undertaken to establish the enantiopurity of a representative cyclohexadiene product.

Details

Item Type Articles
CreatorsAli Khan, M., Mahon, M. F., Lowe, J. P., Stewart, A. J. W. and Lewis, S. E.
DOI10.1002/chem.201202411
Related URLs
URLURL Type
http://www.scopus.com/inward/record.url?scp=84867200214&partnerID=8YFLogxKUNSPECIFIED
DepartmentsFaculty of Science > Chemistry
Research CentresCentre for Sustainable Chemical Technologies
RefereedYes
StatusPublished
ID Code32772

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