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

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.
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Submitted on : Monday, September 4, 2017 - 2:38:38 PM
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D.M. Carminati, D. Intrieri, S. Le Gac, T. Roisnel, B. Boitrel, et al.. Synthesis, characterisation and catalytic use of iron porphyrin amino ester conjugates. New Journal of Chemistry, Royal Society of Chemistry, 2017, 41 (13), pp.5950--5959. ⟨10.1039/c7nj01189j⟩. ⟨hal-01581220⟩

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