Iron(0) Tricarbonyl Complexes of Microbially Derived Cyclohexadiene Ligands Containing Quaternary Stereocenters

Khan, Monika Ali; Mahon, Mary F.; Stewart, Alan J. W.; Lewis, Simon E.

doi:10.1021/om9009069

Cited by 23 publications

(2 citation statements)

References 72 publications

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“…The precursor for complex 1 , diene 2 , could be synthesized via a cycloaddition reaction between an acrylate ester and furan, both available from biorenewable sources (Scheme ). − Alternatively, structurally similar dienes can also be made via biocatalytic cis -dihydroxylation of aromatic molecules, and these have been exploited using iron carbonyl chemistry. ,− …”

Section: Results and Discussionmentioning

confidence: 99%

Selective Iron-Mediated C- and O-Addition of Phenolic Nucleophiles to a Cyclohexadiene Scaffold Using Renewable Precursors

Dunås

Paterson

Kociok‐Köhn

et al. 2019

ACS Sustainable Chem. Eng.

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Renewable phenols have been investigated as nucleophiles for the addition to a cationic cyclohexadienyl iron carbonyl scaffold. Benign conditions compatible with solvents such as ethanol and water were developed, and for the first time, selective C- or O-addition could be achieved. In addition, a novel atom-economic approach to forming the C-addition products directly from the neutral precursor complex in a single step using a catalytic acid is described. The formed C-addition product could then be selectively demetalated to form one of two different product classes, a functionalized arene or a cyclohexadiene.

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Section: Results and Discussionmentioning

confidence: 99%

Selective Iron-Mediated C- and O-Addition of Phenolic Nucleophiles to a Cyclohexadiene Scaffold Using Renewable Precursors

Dunås

Paterson

Kociok‐Köhn

et al. 2019

ACS Sustainable Chem. Eng.

Self Cite

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“…We have recently explored iron diene complexation in the context of ipso-ortho arene dihydrodiol 4 and its derivatives and found that complexation of a tricarbonyliron fragment to methyl ester 7 affords solely the isomer in which the hydroxyls are endo and the ester is exo ( 8 , Scheme 3 ) [ 45 ]. This result is noteworthy, since in contrast to 5 , ligand 7 presents Lewis basic functionality on both sides of the ring.…”

Section: Introductionmentioning

confidence: 99%