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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Molecular Diversity Preservation International
2009
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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. |
format | Online Article Text |
id | pubmed-6255108 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | Molecular Diversity Preservation International |
record_format | MEDLINE/PubMed |
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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