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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...
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/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. |
format | Online Article Text |
id | pubmed-9024675 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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