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Article: Iron-Catalyzed Highly Enantioselective cis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2

TitleIron-Catalyzed Highly Enantioselective cis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2
Authors
Keywordsnitrogen ligands
trisubstituted alkenes
hydroxylation
iron
homogeneous catalysis
Issue Date2020
PublisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at https://onlinelibrary.wiley.com/journal/15213773
Citation
Angewandte Chemie (International Edition), 2020, v. 59, n. 38, p. 16561-16571 How to Cite?
Abstract© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Reliable methods for enantioselective cis-dihydroxylation of trisubstituted alkenes are scarce. The iron(II) complex cis-α-[FeII(2-Me2-BQPN)(OTf)2], which bears a tetradentate N4 ligand (Me2-BQPN=(R,R)-N,N′-dimethyl-N,N′-bis(2-methylquinolin-8-yl)-1,2-diphenylethane-1,2-diamine), was prepared and characterized. With this complex as the catalyst, a broad range of trisubstituted electron-deficient alkenes were efficiently oxidized to chiral cis-diols in yields of up to 98 % and up to 99.9 % ee when using hydrogen peroxide (H2O2) as oxidant under mild conditions. Experimental studies (including 18O-labeling, ESI-MS, NMR, EPR, and UV/Vis analyses) and DFT calculations were performed to gain mechanistic insight, which suggested possible involvement of a chiral cis-FeV(O)2 reaction intermediate as an active oxidant. This cis-[FeII(chiral N4 ligand)]2+/H2O2 method could be a viable green alternative/complement to the existing OsO4-based methods for asymmetric alkene dihydroxylation reactions.
Persistent Identifierhttp://hdl.handle.net/10722/288822
ISSN
2019 Impact Factor: 12.959
2015 SCImago Journal Rankings: 6.229

 

DC FieldValueLanguage
dc.contributor.authorWei, Jinhu-
dc.contributor.authorWu, Liangliang-
dc.contributor.authorWang, Hai Xu-
dc.contributor.authorZhang, Xiting-
dc.contributor.authorTse, Chun Wai-
dc.contributor.authorZhou, Cong Ying-
dc.contributor.authorHuang, Jie Sheng-
dc.contributor.authorChe, Chi Ming-
dc.date.accessioned2020-10-12T08:05:58Z-
dc.date.available2020-10-12T08:05:58Z-
dc.date.issued2020-
dc.identifier.citationAngewandte Chemie (International Edition), 2020, v. 59, n. 38, p. 16561-16571-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/288822-
dc.description.abstract© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Reliable methods for enantioselective cis-dihydroxylation of trisubstituted alkenes are scarce. The iron(II) complex cis-α-[FeII(2-Me2-BQPN)(OTf)2], which bears a tetradentate N4 ligand (Me2-BQPN=(R,R)-N,N′-dimethyl-N,N′-bis(2-methylquinolin-8-yl)-1,2-diphenylethane-1,2-diamine), was prepared and characterized. With this complex as the catalyst, a broad range of trisubstituted electron-deficient alkenes were efficiently oxidized to chiral cis-diols in yields of up to 98 % and up to 99.9 % ee when using hydrogen peroxide (H2O2) as oxidant under mild conditions. Experimental studies (including 18O-labeling, ESI-MS, NMR, EPR, and UV/Vis analyses) and DFT calculations were performed to gain mechanistic insight, which suggested possible involvement of a chiral cis-FeV(O)2 reaction intermediate as an active oxidant. This cis-[FeII(chiral N4 ligand)]2+/H2O2 method could be a viable green alternative/complement to the existing OsO4-based methods for asymmetric alkene dihydroxylation reactions.-
dc.languageeng-
dc.publisherWiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at https://onlinelibrary.wiley.com/journal/15213773-
dc.relation.ispartofAngewandte Chemie (International Edition)-
dc.subjectnitrogen ligands-
dc.subjecttrisubstituted alkenes-
dc.subjecthydroxylation-
dc.subjectiron-
dc.subjecthomogeneous catalysis-
dc.titleIron-Catalyzed Highly Enantioselective cis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/anie.202002866-
dc.identifier.pmid32500643-
dc.identifier.scopuseid_2-s2.0-85087995007-
dc.identifier.hkuros317302-
dc.identifier.volume59-
dc.identifier.issue38-
dc.identifier.spage16561-
dc.identifier.epage16571-
dc.identifier.eissn1521-3773-

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