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- Publisher Website: 10.1002/anie.202002866
- Scopus: eid_2-s2.0-85087995007
- PMID: 32500643
- WOS: WOS:000548332500001
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Article: Iron-Catalyzed Highly Enantioselective cis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2
Title | Iron-Catalyzed Highly Enantioselective cis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2 |
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Authors | |
Keywords | nitrogen ligands trisubstituted alkenes hydroxylation iron homogeneous catalysis |
Issue Date | 2020 |
Publisher | Wiley - 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 Identifier | http://hdl.handle.net/10722/288822 |
ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Wei, Jinhu | - |
dc.contributor.author | Wu, Liangliang | - |
dc.contributor.author | Wang, Hai Xu | - |
dc.contributor.author | Zhang, Xiting | - |
dc.contributor.author | Tse, Chun Wai | - |
dc.contributor.author | Zhou, Cong Ying | - |
dc.contributor.author | Huang, Jie Sheng | - |
dc.contributor.author | Che, Chi Ming | - |
dc.date.accessioned | 2020-10-12T08:05:58Z | - |
dc.date.available | 2020-10-12T08:05:58Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Angewandte Chemie (International Edition), 2020, v. 59, n. 38, p. 16561-16571 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://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.language | eng | - |
dc.publisher | Wiley - VCH Verlag GmbH & Co. KGaA. The Journal's web site is located at https://onlinelibrary.wiley.com/journal/15213773 | - |
dc.relation.ispartof | Angewandte Chemie (International Edition) | - |
dc.subject | nitrogen ligands | - |
dc.subject | trisubstituted alkenes | - |
dc.subject | hydroxylation | - |
dc.subject | iron | - |
dc.subject | homogeneous catalysis | - |
dc.title | Iron-Catalyzed Highly Enantioselective cis-Dihydroxylation of Trisubstituted Alkenes with Aqueous H2O2 | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/anie.202002866 | - |
dc.identifier.pmid | 32500643 | - |
dc.identifier.scopus | eid_2-s2.0-85087995007 | - |
dc.identifier.hkuros | 317302 | - |
dc.identifier.volume | 59 | - |
dc.identifier.issue | 38 | - |
dc.identifier.spage | 16561 | - |
dc.identifier.epage | 16571 | - |
dc.identifier.eissn | 1521-3773 | - |
dc.identifier.isi | WOS:000548332500001 | - |
dc.identifier.issnl | 1433-7851 | - |