Manganese Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Amides with H2O2 ArticleGenre_short.SHORT_COMMUNICATION
| Journal |
Advanced Synthesis and Catalysis
ISSN: 1615-4150 , E-ISSN: 1615-4169 |
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| Output data | Year: 2021, Volume: 363, Number: 11, Pages: 2778-2782 Pages count : 5 DOI: 10.1002/adsc.202100198 | ||
| Tags | Enantioselective; Epoxidation; Manganese; Enamide; Hydrogen Peroxide | ||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Ministry of Science and Higher Education of the Russian Federation | 0239-2021-0009 |
Abstract:
Herewith, we report the enantioselective epoxidation of electron-deficient cis- and trans-alpha,beta-unsaturated amides with the environmentally benign oxidant H2O2. The catalysts - manganese complexes with bis-amino-bis-pyridine and structurally related ligands - exhibit reasonably high efficiency (up to 100 TON) and excellent chemo- and enantioselectivity (up to 100% and 99% ee, respectively). Crucially, the cis-enamides epoxidation enantioselectivity and yield are dramatically enhanced by the presence of NH-moiety, which effect can be explained by the hydrogen bonding interaction between the cis-enamide substrate and the manganese based oxygen transferring species.
Cite:
Ottenbacher R.V.
, Kurganskiy V.I.
, Talsi E.P.
, Bryliakov K.P.
Manganese Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Amides with H2O2
Advanced Synthesis and Catalysis. 2021. V.363. N11. P.2778-2782. DOI: 10.1002/adsc.202100198 WOS Scopus РИНЦ AN OpenAlex
Manganese Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Amides with H2O2
Advanced Synthesis and Catalysis. 2021. V.363. N11. P.2778-2782. DOI: 10.1002/adsc.202100198 WOS Scopus РИНЦ AN OpenAlex
Dates:
| Submitted: | Feb 11, 2021 |
| Accepted: | Apr 12, 2021 |
| Published online: | Apr 15, 2021 |
| Published print: | Jun 8, 2021 |
Identifiers:
| Web of science: | WOS:000642637600001 |
| Scopus: | 2-s2.0-85104808831 |
| Elibrary: | 46022395 |
| Chemical Abstracts: | 2021:956111 |
| OpenAlex: | W3155106535 |