Synthesis, characterisation and catalytic use of iron porphyrin amino ester conjugates. (9th June 2017)

• Record Type: Journal Article
• Authors: Carminati, Daniela M.; Intrieri, Daniela; Le Gac, Stéphane; Roisnel, Thierry; Boitrel, Bernard; Toma, Lucio; Legnani, Laura; Gallo, Emma
• Is Part Of: New journal of chemistry. Volume 41:Number 13(2017)
• Page Start: 5950
• Page End: 5959
• Publication Date: 2017-06-09
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c7nj01189j
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : This study described the synthesis and characterisation of C 2 -symmetrical chiral Fe(iii )(porphyrin)(OMe) complexes, whose activity as cyclopropanation catalysts was investigated from both experimental and theoretical viewpoints. Abstract : The present study deals with the synthesis and characterisation of C 2 -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.