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Asymmetric epoxidation with H2O2 by manipulating the electronic properties of non-heme iron catalysts

A non-heme iron complex that catalyzes highly enantioselective epoxidation of olefins with H2O2 is described. Improvement of enantiomeric excesses is attained by the use of catalytic amounts of carboxylic acid additives. Electronic effects imposed by the ligand on the iron center are shown to synergistically cooperate with catalytic amounts of carboxylic acids in promoting efficient O-O cleavage and creating highly chemo-and enantioselective epoxidizing species which provide a broad range of epoxides in synthetically valuable yields and short reaction times

We acknowledge financial support from European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, Consolider-Ingenio CSD2010-00065), and the Catalan DIUE of the Generalitat de Catalunya (2009SGR637). J.Ll.-F. thanks MICINN for a RyC contract. X.R. and M.C. acknowledge ICREA-Academia awards. X.R. is grateful for financial support from INNPLAN-TA Project No. IPN-2011-0059-PCT-42000-ACT1. I.G.-B. thanks the European Community for an IOF Marie Curie fellowship. We acknowledge STRs from UdG for technical support

info:eu-repo/grantAgreement/MINECO//CTQ2012-37420-C02-01/ES/DISEÑO BIOINSPIRADO DE CATALIZADORES PARA LA OXIDACION DE ENLACES C-H, C=C Y AGUA/

American Chemical Society (ACS)

Manager: European Research Council
Ministerio de Economía y Competitividad (Espanya)
Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d’Ajuts Universitaris i de Recerca
Author: Cussó Forest, Olaf
Garcia Bosch, Isaac
Ribas Salamaña, Xavi
Lloret Fillol, Julio
Costas Salgueiro, Miquel
Abstract: A non-heme iron complex that catalyzes highly enantioselective epoxidation of olefins with H2O2 is described. Improvement of enantiomeric excesses is attained by the use of catalytic amounts of carboxylic acid additives. Electronic effects imposed by the ligand on the iron center are shown to synergistically cooperate with catalytic amounts of carboxylic acids in promoting efficient O-O cleavage and creating highly chemo-and enantioselective epoxidizing species which provide a broad range of epoxides in synthetically valuable yields and short reaction times
We acknowledge financial support from European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, Consolider-Ingenio CSD2010-00065), and the Catalan DIUE of the Generalitat de Catalunya (2009SGR637). J.Ll.-F. thanks MICINN for a RyC contract. X.R. and M.C. acknowledge ICREA-Academia awards. X.R. is grateful for financial support from INNPLAN-TA Project No. IPN-2011-0059-PCT-42000-ACT1. I.G.-B. thanks the European Community for an IOF Marie Curie fellowship. We acknowledge STRs from UdG for technical support
Format: application/pdf
Document access: http://hdl.handle.net/10256/10022
Language: eng
Publisher: American Chemical Society (ACS)
Collection: info:eu-repo/semantics/altIdentifier/doi/10.1021/ja4078446
info:eu-repo/semantics/altIdentifier/issn/0002-7863
info:eu-repo/semantics/altIdentifier/eissn/1520-5126
MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2009-2014/2009 SGR-637
info:eu-repo/grantAgreement/EC/FP7/239910/EU/Bio-inspired Design of Catalysts for Selective Oxidations of C-H and C=C Bonds/BIDECASEOX
Is part of: info:eu-repo/grantAgreement/MINECO//CTQ2012-37420-C02-01/ES/DISEÑO BIOINSPIRADO DE CATALIZADORES PARA LA OXIDACION DE ENLACES C-H, C=C Y AGUA/
Rights: Tots els drets reservats
Subject: Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Compostos heterocíclics
Heterocyclic compounds
Title: Asymmetric epoxidation with H2O2 by manipulating the electronic properties of non-heme iron catalysts
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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