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H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters

In this work, we would like to present the development of a highly optimized method for generating the quaternary stereogenic centers in β-keto esters. This enantioselective phase-transfer alkylation catalyzed by hybrid Cinchona catalysts allows for the efficient generation of the optically active p...

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Detalles Bibliográficos
Autores principales: Niedbała, Patryk, Majdecki, Maciej, Grodek, Piotr, Jurczak, Janusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9024675/
https://www.ncbi.nlm.nih.gov/pubmed/35458707
http://dx.doi.org/10.3390/molecules27082508
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author Niedbała, Patryk
Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
author_facet Niedbała, Patryk
Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
author_sort Niedbała, Patryk
collection PubMed
description In this work, we would like to present the development of a highly optimized method for generating the quaternary stereogenic centers in β-keto esters. This enantioselective phase-transfer alkylation catalyzed by hybrid Cinchona catalysts allows for the efficient generation of the optically active products with excellent enantioselectivity, using only 1 mol% of the catalyst. The vast majority of phase-transfer catalysts in asymmetric synthesis work by creating ionic pairs with the nucleophile-attacking anionic substrate. Therefore, it is a sensible approach to search for new methodologies capable of introducing functional groups into the precursor’s structure, maintaining high yields and enantiomeric purity.
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spelling pubmed-90246752022-04-23 H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters Niedbała, Patryk Majdecki, Maciej Grodek, Piotr Jurczak, Janusz Molecules Article In this work, we would like to present the development of a highly optimized method for generating the quaternary stereogenic centers in β-keto esters. This enantioselective phase-transfer alkylation catalyzed by hybrid Cinchona catalysts allows for the efficient generation of the optically active products with excellent enantioselectivity, using only 1 mol% of the catalyst. The vast majority of phase-transfer catalysts in asymmetric synthesis work by creating ionic pairs with the nucleophile-attacking anionic substrate. Therefore, it is a sensible approach to search for new methodologies capable of introducing functional groups into the precursor’s structure, maintaining high yields and enantiomeric purity. MDPI 2022-04-13 /pmc/articles/PMC9024675/ /pubmed/35458707 http://dx.doi.org/10.3390/molecules27082508 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 Article
Niedbała, Patryk
Majdecki, Maciej
Grodek, Piotr
Jurczak, Janusz
H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
title H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
title_full H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
title_fullStr H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
title_full_unstemmed H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
title_short H-Bond Mediated Phase-Transfer Catalysis: Enantioselective Generating of Quaternary Stereogenic Centers in β-Keto Esters
title_sort h-bond mediated phase-transfer catalysis: enantioselective generating of quaternary stereogenic centers in β-keto esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9024675/
https://www.ncbi.nlm.nih.gov/pubmed/35458707
http://dx.doi.org/10.3390/molecules27082508
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