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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

© Journal of the American Chemical Society, 2013, vol. 135, núm. 39, p. 14871-14878

American Chemical Society (ACS)

Autor: Cussó Forest, Olaf
Garcia Bosch, Isaac
Ribas Salamaña, Xavi
Lloret Fillol, Julio
Costas Salgueiro, Miquel
Data: 2013
Resum: 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
ISSN: 0002-7863 (versió paper)
1520-5126 (versió electrònica)
Accés al document: http://hdl.handle.net/10256/10022
Llenguatge: eng
Editor: American Chemical Society (ACS)
Col·lecció: MINECO/PN 2013-2015/CTQ2012-37420-C02-01
MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2009-2014/2009 SGR-637
Reproducció digital del document publicat a: http://dx.doi.org/10.1021/ja4078446
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/239910
És part de: © Journal of the American Chemical Society, 2013, vol. 135, núm. 39, p. 14871-14878
Drets: Tots els drets reservats
Matèria: Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Compostos heterocíclics
Heterocyclic compounds
Títol: Asymmetric epoxidation with H2O2 by manipulating the electronic properties of non-heme iron catalysts
Tipus: info:eu-repo/semantics/article
Repositori: DUGiDocs

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