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Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes
Asymmetric epoxidation of a series of olefinic substrates with sodium percarbonate oxidant in the presence of homogeneous catalysts based on Mn complexes with bis-amino-bis-pyridine ligands is reported. Sodium percarbonate is a readily available and environmentally benign oxidant that is studied in...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9027068/ https://www.ncbi.nlm.nih.gov/pubmed/35458734 http://dx.doi.org/10.3390/molecules27082538 |
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author | Drozd, Varvara A. Ottenbacher, Roman V. Bryliakov, Konstantin P. |
author_facet | Drozd, Varvara A. Ottenbacher, Roman V. Bryliakov, Konstantin P. |
author_sort | Drozd, Varvara A. |
collection | PubMed |
description | Asymmetric epoxidation of a series of olefinic substrates with sodium percarbonate oxidant in the presence of homogeneous catalysts based on Mn complexes with bis-amino-bis-pyridine ligands is reported. Sodium percarbonate is a readily available and environmentally benign oxidant that is studied in these reactions for the first time. The epoxidation proceeded with good to high yields (up to 100%) and high enantioselectivities (up to 99% ee) using as low as 0.2 mol. % catalyst loadings. The epoxidation protocol is suitable for various types of substrates, including unfunctionalized alkenes, α,β-unsaturated ketones, esters (cis- and trans-), and amides (cis- and trans-). The reaction mechanism is discussed. |
format | Online Article Text |
id | pubmed-9027068 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-90270682022-04-23 Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes Drozd, Varvara A. Ottenbacher, Roman V. Bryliakov, Konstantin P. Molecules Communication Asymmetric epoxidation of a series of olefinic substrates with sodium percarbonate oxidant in the presence of homogeneous catalysts based on Mn complexes with bis-amino-bis-pyridine ligands is reported. Sodium percarbonate is a readily available and environmentally benign oxidant that is studied in these reactions for the first time. The epoxidation proceeded with good to high yields (up to 100%) and high enantioselectivities (up to 99% ee) using as low as 0.2 mol. % catalyst loadings. The epoxidation protocol is suitable for various types of substrates, including unfunctionalized alkenes, α,β-unsaturated ketones, esters (cis- and trans-), and amides (cis- and trans-). The reaction mechanism is discussed. MDPI 2022-04-14 /pmc/articles/PMC9027068/ /pubmed/35458734 http://dx.doi.org/10.3390/molecules27082538 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Communication Drozd, Varvara A. Ottenbacher, Roman V. Bryliakov, Konstantin P. Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes |
title | Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes |
title_full | Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes |
title_fullStr | Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes |
title_full_unstemmed | Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes |
title_short | Asymmetric Epoxidation of Olefins with Sodium Percarbonate Catalyzed by Bis-amino-bis-pyridine Manganese Complexes |
title_sort | asymmetric epoxidation of olefins with sodium percarbonate catalyzed by bis-amino-bis-pyridine manganese complexes |
topic | Communication |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9027068/ https://www.ncbi.nlm.nih.gov/pubmed/35458734 http://dx.doi.org/10.3390/molecules27082538 |
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