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

Monika Ali Khan, Mary F. Mahon, John P. Lowe, Alan J. W. Stewart, Simon E. Lewis

Research output: Contribution to journalArticle

17 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)13480-13493
Number of pages14
JournalChemistry - A European Journal
Volume18
Issue number42
Early online date13 Sep 2012
DOIs
Publication statusPublished - 15 Oct 2012

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