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Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis

Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. Th...

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Detalles Bibliográficos
Autores principales: Cafeo, Grazia, De Rosa, Margherita, Kohnke, Franz H., Soriente, Annunziata, Talotta, Carmen, Valenti, Luca
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255108/
https://www.ncbi.nlm.nih.gov/pubmed/19633626
http://dx.doi.org/10.3390/molecules14072594
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author Cafeo, Grazia
De Rosa, Margherita
Kohnke, Franz H.
Soriente, Annunziata
Talotta, Carmen
Valenti, Luca
author_facet Cafeo, Grazia
De Rosa, Margherita
Kohnke, Franz H.
Soriente, Annunziata
Talotta, Carmen
Valenti, Luca
author_sort Cafeo, Grazia
collection PubMed
description Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The γ-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction.
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spelling pubmed-62551082018-11-30 Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis Cafeo, Grazia De Rosa, Margherita Kohnke, Franz H. Soriente, Annunziata Talotta, Carmen Valenti, Luca Molecules Article Calix[4]pyrrole (1), calix[2]m-benzo[4]pyrrole (2), 10α,20β- and 10α,20α- bis(4-nitrophenyl)-calix[4]pyrroles 3 and 4, respectively, were found to exhibit various organocatalytic activities in the diastereoselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF, 7) to aldehydes. The γ-hydroxybutenolide products are obtained in fairly good yields and with moderate diastereoselectivity. The structures of the catalysts, as well as the reaction conditions, strongly influence the efficiency of the reaction. Molecular Diversity Preservation International 2009-07-15 /pmc/articles/PMC6255108/ /pubmed/19633626 http://dx.doi.org/10.3390/molecules14072594 Text en © 2009 by the authors. Licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Cafeo, Grazia
De Rosa, Margherita
Kohnke, Franz H.
Soriente, Annunziata
Talotta, Carmen
Valenti, Luca
Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
title Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
title_full Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
title_fullStr Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
title_full_unstemmed Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
title_short Calixpyrrole Derivatives: “Multi Hydrogen Bond” Catalysts for γ-Butenolide Synthesis
title_sort calixpyrrole derivatives: “multi hydrogen bond” catalysts for γ-butenolide synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255108/
https://www.ncbi.nlm.nih.gov/pubmed/19633626
http://dx.doi.org/10.3390/molecules14072594
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