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Issue 18, 2019
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Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand

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Abstract

The chiral tetradentate N4-donor ligand, 1-methyl-2-({(S)-2-[(S)-1-(1-methylbenzimidazol-2-yl methyl)pyrrolidin-2-yl]pyrrolidin-1-yl}methyl) benzimidazole (S,S-PDBzL), based on a chiral dipyrrolidine backbone, has been synthesized and its corresponding Fe(II) complex has been prepared and characterized. The X-ray structure of the complex reveals that the Fe(II) ion is in a distorted octahedral coordination environment with two cis-oriented coordination sites occupied by (labile) triflate anions. The ability of the iron complex to catalyze asymmetric epoxidation reactions of olefins with H2O2 was investigated, using 2-cyclohexen-1-one, 2-cyclopenten-1-one, cis-β-methylstyrene, isophorone, chalcones and tetralones as substrates. Different carboxylic acids were used as additives to enhance yields and enantioselectivities, and 2-ethylhexanoic acid was found to give the best results. The catalysis results indicate that the Fe(II) complex is capable of effecting comparatively high enantioselectivities (>80%) in the epoxidation reactions.

Graphical abstract: Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(ii) catalyst of a chiral tetradentate ligand

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Publication details

The article was received on 08 Nov 2018, accepted on 15 Mar 2019 and first published on 05 Apr 2019


Article type: Paper
DOI: 10.1039/C8DT04449J
Dalton Trans., 2019,48, 6123-6131
  • Open access: Creative Commons BY-NC license
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    Highly enantioselective epoxidation of olefins by H2O2 catalyzed by a non-heme Fe(II) catalyst of a chiral tetradentate ligand

    M. Mitra, O. Cusso, S. S. Bhat, M. Sun, M. Cianfanelli, M. Costas and E. Nordlander, Dalton Trans., 2019, 48, 6123
    DOI: 10.1039/C8DT04449J

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