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EnglishThe direct transformation of lactam-, lactone-, and thiolactone-derived triflates into N-methoxy-N-methyl or morpholine Weinreb amides has been realized using Pd-catalyzed aminocarbonylation under CO atmospheric pressure and at room temperature. The carbonylative coupling can be efficiently carried out with 2% of catalyst in the presence of Xantphos as a ligand. The amides smoothly react with nucleophiles to afford acylated aza-, oxa- and thio-heterocyles. The proposed methodology could be advantageously exploited for the synthesis of dienones in which one of the double bonds is embedded in a heterocyclic moiety, as useful substrates for Nazarov cyclization.
| Titolo: | Synthesis of Weinreb amides via Pd-catalyzed aminocarbonylation of heterocyclic-derived triflates |
| Autori Riconosciuti: | |
| Autori: | A. Deagostino; P. Larini; E. G. Occhiato; L. Pizzuto; C. Prandi; P. Venturello |
| Data di pubblicazione: | 2008 |
| Abstract: | The direct transformation of lactam-, lactone-, and thiolactone-derived triflates into N-methoxy-N-methyl or morpholine Weinreb amides has been realized using Pd-catalyzed aminocarbonylation under CO atmospheric pressure and at room temperature. The carbonylative coupling can be efficiently carried out with 2% of catalyst in the presence of Xantphos as a ligand. The amides smoothly react with nucleophiles to afford acylated aza-, oxa- and thio-heterocyles. The proposed methodology could be advantageously exploited for the synthesis of dienones in which one of the double bonds is embedded in a heterocyclic moiety, as useful substrates for Nazarov cyclization. |
| Volume: | 73 |
| Pagina iniziale: | 1941 |
| Pagina finale: | 1945 |
| Digital Object Identifier (DOI): | 10.1021/jo7024898 |
| Rivista: | JOURNAL OF ORGANIC CHEMISTRY |
| Appare nelle tipologie: | 03A-Articolo su Rivista |
File in questo prodotto:
| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| Joc article.pdf | articolo principale | 1 Ver. finale autore | Open Access Visualizza/Apri | |
| JOC2008Prandi.pdf | 2 PDF Editoriale | Utenti riconosciuti Richiedi una copia |
http://hdl.handle.net/2318/41423
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