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Synergistic Interplay of a Non-Heme Iron Catalyst and Amino Acid Coligands in H2O2 Activation for Asymmetric Epoxidation of α-Alkyl-Substituted Styrenes

Highly enantioselective epoxidation of α-substituted styrenes with aqueous H2O2 is described by using a chiral iron complex as the catalyst and N-protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H2O2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities (up to 97 % ee) in short reaction times

We acknowledge group LIPPSO from UdG for providing amino acid samples and A. Riera (IRB) for access to a polarimeter. We acknowledge financial support from the European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, CSD2010-00065), and Generalitat de Catalunya (2009SGR637). J.L.-F. thanks MICINN for a RyC contract. X.R. and M.C. thank ICREA-Academia awards

© Angewandte Chemie-International Edition, 2015, vol. 54, núm. 9, p. 2729–2733

Wiley-VCH Verlag

Author: Cussó, Olaf
Ribas Salamaña, Xavi
Lloret Fillol, Julio
Costas Salgueiro, Miquel
Date: 2015
Abstract: Highly enantioselective epoxidation of α-substituted styrenes with aqueous H2O2 is described by using a chiral iron complex as the catalyst and N-protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H2O2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities (up to 97 % ee) in short reaction times
We acknowledge group LIPPSO from UdG for providing amino acid samples and A. Riera (IRB) for access to a polarimeter. We acknowledge financial support from the European Research Council (ERC-2009-StG-239910), MINECO of Spain (CTQ2012-37420-C02-01/BQU, CSD2010-00065), and Generalitat de Catalunya (2009SGR637). J.L.-F. thanks MICINN for a RyC contract. X.R. and M.C. thank ICREA-Academia awards
Format: application/pdf
ISSN: 1433-7851 (versió paper)
1521-3773 (versió electrònica)
Document access: http://hdl.handle.net/10256/12060
Language: eng
Publisher: Wiley-VCH Verlag
Collection: 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/10.1002/anie.201410557
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/239910
Is part of: © Angewandte Chemie-International Edition, 2015, vol. 54, núm. 9, p. 2729–2733
Rights: Tots els drets reservats
Subject: Aminoàcids
Amino acids
Catàlisi asimètrica
Enantioselective catalysis
Title: Synergistic Interplay of a Non-Heme Iron Catalyst and Amino Acid Coligands in H2O2 Activation for Asymmetric Epoxidation of α-Alkyl-Substituted Styrenes
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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