Biomimetic Non-Heme Iron-Catalyzed Epoxidation of Challenging Terminal Alkenes Using Aqueous H
enantioselective epoxidation
hydrogen peroxide oxidant
non-heme iron-catalysis
peptide-like ligands
terminal olefins
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
01 Sep 2019
01 Sep 2019
Historique:
received:
10
06
2019
revised:
20
08
2019
accepted:
23
08
2019
entrez:
5
9
2019
pubmed:
5
9
2019
medline:
31
1
2020
Statut:
epublish
Résumé
Catalysis mediated by iron complexes is emerging as an eco-friendly and inexpensive option in comparison to traditional metal catalysis. The epoxidation of alkenes constitutes an attractive application of iron(III) catalysis, in which terminal olefins are challenging substrates. Herein, we describe our study on the design of biomimetic non-heme ligands for the in situ generation of iron(III) complexes and their evaluation as potential catalysts in epoxidation of terminal olefins. Since it is well-known that active sites of oxidases might involve imidazole fragment of histidine, various simple imidazole derivatives (seven compounds) were initially evaluated in order to find the best reaction conditions and to develop, subsequently, more elaborated amino acid-derived peptide-like chiral ligands (10 derivatives) for enantioselective epoxidations.
Identifiants
pubmed: 31480640
pii: molecules24173182
doi: 10.3390/molecules24173182
pmc: PMC6749192
pii:
doi:
Substances chimiques
Alkenes
0
Epoxy Compounds
0
Imidazoles
0
Ligands
0
Oxidants
0
Peptides
0
Heme
42VZT0U6YR
Hydrogen Peroxide
BBX060AN9V
Iron
E1UOL152H7
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Consejo Nacional de Ciencia y Tecnología, Mexico
ID : 220945
Déclaration de conflit d'intérêts
The authors declare no conflicts of interest.
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