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Highly enantioselective epoxidation of olefins by H 2 O 2 catalyzed by a non-heme Fe(ii) catalyst of a chiral tetradentate ligand

Mitra, Mainak LU ; Cusso, Olaf; Bhat, Satish S. LU ; Sun, Mingzhe LU ; Cianfanelli, Marco; Costas, Miquel and Nordlander, Ebbe LU (2019) In Dalton Transactions 48(18). p.6123-6131
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-
PDBz
L), 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... (More)


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-
PDBz
L), 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 H
2
O
2
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.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Dalton Transactions
volume
48
issue
18
pages
9 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85065503069
ISSN
1477-9226
DOI
10.1039/c8dt04449j
language
English
LU publication?
yes
id
b8b437c5-3a04-44b2-b64e-16142bd82931
date added to LUP
2019-06-03 14:26:52
date last changed
2019-09-08 04:40:48
@article{b8b437c5-3a04-44b2-b64e-16142bd82931,
  abstract     = {<p><br>
                                                         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-                             <br>
                            <sup>PDBz</sup><br>
                                                         L), 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 H                             <br>
                            <sub>2</sub><br>
                                                         O                             <br>
                            <sub>2</sub><br>
                                                          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 (&gt;80%) in the epoxidation reactions.                         <br>
                        </p>},
  author       = {Mitra, Mainak and Cusso, Olaf and Bhat, Satish S. and Sun, Mingzhe and Cianfanelli, Marco and Costas, Miquel and Nordlander, Ebbe},
  issn         = {1477-9226},
  language     = {eng},
  number       = {18},
  pages        = {6123--6131},
  publisher    = {Royal Society of Chemistry},
  series       = {Dalton Transactions},
  title        = {Highly enantioselective epoxidation of olefins by H                         
                        <sub>2</sub>
                                                 O                         
                        <sub>2</sub>
                                                  catalyzed by a non-heme Fe(ii) catalyst of a chiral tetradentate ligand},
  url          = {http://dx.doi.org/10.1039/c8dt04449j},
  volume       = {48},
  year         = {2019},
}