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The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives
This work involves the synthesis and subsequent development of a number of novel organocatalysts generated from β-amino acids bearing diendo and diexo norbornene skeletons to improve their catalytic characteristics. The aldol reaction between isatin and acetone selected as the model reaction, was us...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10292165/ https://www.ncbi.nlm.nih.gov/pubmed/37377868 http://dx.doi.org/10.1039/d3ra03528j |
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author | Faragó, Tünde Remete, Attila M. Szatmári, István Ambrus, Rita Palkó, Márta |
author_facet | Faragó, Tünde Remete, Attila M. Szatmári, István Ambrus, Rita Palkó, Márta |
author_sort | Faragó, Tünde |
collection | PubMed |
description | This work involves the synthesis and subsequent development of a number of novel organocatalysts generated from β-amino acids bearing diendo and diexo norbornene skeletons to improve their catalytic characteristics. The aldol reaction between isatin and acetone selected as the model reaction, was used to test and study enantioselectivities. The potential impact on enantioselectivity control regarding enantiomeric excess (ee%) was probed by varying the reaction parameters, such as additive, solvent, catalyst loading, temperature and substrate range. The corresponding 3-hydroxy-3-alkyl-2-oxindole derivetives were produced by organocatalyst 7 with good enantioselectivity up to 57% ee in the presence of LiOH. Substrate screening was used to investigate a number of substituted isatins with excellent findings up to 99% ee. Another aspect of this effort involved employing high-speed ball mill apparatus to conduct a mechanochemical study to make this model reaction more environmentally benign and sustainable. |
format | Online Article Text |
id | pubmed-10292165 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-102921652023-06-27 The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives Faragó, Tünde Remete, Attila M. Szatmári, István Ambrus, Rita Palkó, Márta RSC Adv Chemistry This work involves the synthesis and subsequent development of a number of novel organocatalysts generated from β-amino acids bearing diendo and diexo norbornene skeletons to improve their catalytic characteristics. The aldol reaction between isatin and acetone selected as the model reaction, was used to test and study enantioselectivities. The potential impact on enantioselectivity control regarding enantiomeric excess (ee%) was probed by varying the reaction parameters, such as additive, solvent, catalyst loading, temperature and substrate range. The corresponding 3-hydroxy-3-alkyl-2-oxindole derivetives were produced by organocatalyst 7 with good enantioselectivity up to 57% ee in the presence of LiOH. Substrate screening was used to investigate a number of substituted isatins with excellent findings up to 99% ee. Another aspect of this effort involved employing high-speed ball mill apparatus to conduct a mechanochemical study to make this model reaction more environmentally benign and sustainable. The Royal Society of Chemistry 2023-06-26 /pmc/articles/PMC10292165/ /pubmed/37377868 http://dx.doi.org/10.1039/d3ra03528j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Faragó, Tünde Remete, Attila M. Szatmári, István Ambrus, Rita Palkó, Márta The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
title | The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
title_full | The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
title_fullStr | The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
title_full_unstemmed | The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
title_short | The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
title_sort | synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10292165/ https://www.ncbi.nlm.nih.gov/pubmed/37377868 http://dx.doi.org/10.1039/d3ra03528j |
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