Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

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.

(Less)
Please use this url to cite or link to this publication:
author
; ; ; ; ; and
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
  • pmid:30951054
  • 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
2025-01-09 13:05:05
@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}},
  doi          = {{10.1039/c8dt04449j}},
  volume       = {{48}},
  year         = {{2019}},
}