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

D.M. Carminati (1) , D. Intrieri (1) , S. Le Gac (2) , T. Roisnel (2) , B. Boitrel (2) , L. Toma , L. Legnani , E. Gallo (1)

1 UNIMI - Università degli Studi di Milano = University of Milan
2 ISCR - Institut des Sciences Chimiques de Rennes

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.

Domains: Chemical Sciences; Catalysis

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, 2017, 41 (13), pp.5950--5959. ⟨10.1039/c7nj01189j⟩. ⟨hal-01581220⟩