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Synthesis, characterisation and catalytic use of iron porphyrin amino ester conjugates

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Abstract

The present study deals with the synthesis and characterisation of C2-symmetrical chiral Fe(III)(porphyrin)(OMe) catalysts; these catalysts display a totem structure, where each section is assigned to have a specific catalytic activity. The chiral portions of the porphyrin ligand are constituted by amino acid residues, which form a chiral cavity by surrounding both faces of the porphyrin plane, as clearly displayed by the X-ray structure of a free-base porphyrin. The Fe(III)(porphyrin)(OMe)-catalysed cyclopropanation of α-methylstyrene by diazo compounds occurred with excellent diastereoselectivities and a modest enantiocontrol. Thus, the obtained catalytic results have been rationalised by performing a DFT investigation and will be fundamental in the future modification of the molecular structure of chiral ligands to improve their catalytic performance.

Graphical abstract: Synthesis, characterisation and catalytic use of iron porphyrin amino ester conjugates

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Publication details

The article was received on 10 Apr 2017, accepted on 21 May 2017 and first published on 22 May 2017


Article type: Paper
DOI: 10.1039/C7NJ01189J
Citation: New J. Chem., 2017, Advance Article
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    Synthesis, characterisation and catalytic use of iron porphyrin amino ester conjugates

    D. M. Carminati, D. Intrieri, S. Le Gac, T. Roisnel, B. Boitrel, L. Toma, L. Legnani and E. Gallo, New J. Chem., 2017, Advance Article , DOI: 10.1039/C7NJ01189J

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