Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions

The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the...

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Autores principales: Avila-Ortiz, C. Gabriela, Díaz-Corona, Lenin, Jiménez-González, Erika, Juaristi, Eusebio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152315/
https://www.ncbi.nlm.nih.gov/pubmed/28796165
http://dx.doi.org/10.3390/molecules22081328
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author Avila-Ortiz, C. Gabriela
Díaz-Corona, Lenin
Jiménez-González, Erika
Juaristi, Eusebio
author_facet Avila-Ortiz, C. Gabriela
Díaz-Corona, Lenin
Jiménez-González, Erika
Juaristi, Eusebio
author_sort Avila-Ortiz, C. Gabriela
collection PubMed
description The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins.
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spelling pubmed-61523152018-11-13 Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions Avila-Ortiz, C. Gabriela Díaz-Corona, Lenin Jiménez-González, Erika Juaristi, Eusebio Molecules Article The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins. MDPI 2017-08-10 /pmc/articles/PMC6152315/ /pubmed/28796165 http://dx.doi.org/10.3390/molecules22081328 Text en © 2017 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Avila-Ortiz, C. Gabriela
Díaz-Corona, Lenin
Jiménez-González, Erika
Juaristi, Eusebio
Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
title Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
title_full Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
title_fullStr Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
title_full_unstemmed Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
title_short Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions
title_sort asymmetric michael addition organocatalyzed by α,β-dipeptides under solvent-free reaction conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6152315/
https://www.ncbi.nlm.nih.gov/pubmed/28796165
http://dx.doi.org/10.3390/molecules22081328
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