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Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2

An iron complex with a C1-symmetric tetradentate N-based ligand catalyzes the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee), under mild conditions and in short reaction times. Evidence is provided that reactions involve an electrophilic oxidant, and this element is employed in performing site selective epoxidation of enones containing two alkene sites

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)

© Journal of the American Chemical Society, 2016, vol.138, núm. 8, p. 2732-2738

American Chemical Society (ACS)

Author: Cussó Forest, Olaf
Cianfanelli, Marco
Ribas Salamaña, Xavi
Klein Gebbink, Robertus J M
Costas Salgueiro, Miquel
Date: 2016 January 22
Abstract: An iron complex with a C1-symmetric tetradentate N-based ligand catalyzes the asymmetric epoxidation of cyclic enones and cyclohexene ketones with aqueous hydrogen peroxide, providing the corresponding epoxides in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee), under mild conditions and in short reaction times. Evidence is provided that reactions involve an electrophilic oxidant, and this element is employed in performing site selective epoxidation of enones containing two alkene sites
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)
Format: application/pdf
ISSN: 0002-7863 (versió paper)
1520-5126 (versió electrònica)
Document access: http://hdl.handle.net/10256/12121
Language: eng
Publisher: American Chemical Society (ACS)
Collection: MINECO/PN 2013-2015/CTQ2012-37420-C02-01
MICINN/PN 2010-2016/CSD2010-00065
AGAUR/2009-2014/2009 SGR-637
Versió postprint del document publicat a: http://dx.doi.org/10.1021/jacs.5b12681
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/239910
Is part of: © Journal of the American Chemical Society, 2016, vol.138, núm. 8, p. 2732-2738
Rights: Tots els drets reservats
Subject: Epòxids
Epoxy compounds
Catalitzadors
Catalysts
Ferro -- Oxidació
Iron -- Oxidation
Catàlisi asimètrica
Enantioselective catalysis
Title: Iron catalyzed highly enantioselective epoxidation of cyclic aliphatic enones with aqueous H2O2
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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