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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...

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Autores principales: Faragó, Tünde, Remete, Attila M., Szatmári, István, Ambrus, Rita, Palkó, Márta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
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.
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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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