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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...

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Autores principales: Drozd, Varvara A., Ottenbacher, Roman V., Bryliakov, Konstantin P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
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.
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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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