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EnglishThe treatment of propargylic acetals with various lithium and mixed lithium–potassium Schlosser reagents, has allowed a one-pot synthesis of (E)-1,3-enynes, 1,3-diynes and allenes, depending on the reaction conditions and the selected base. Various reaction conditions were investigated in order to control the selectivity of the reactions and to obtain pure products. The metallation–elimination sequence in the presence of a suitable electrophile has provided a linear route to functionalized (E)-conjugated enynes, diynes and allenes.
| Titolo: | Rapid and Easy Access to (E)-1,3-Enynes, 1,3-Diynes and Allenes Starting from Propargylic Acetals, Exploiting the Different Reactivity of Lithium and Mixed Lithium-Potassium Organometallic Reagents |
| Autori Riconosciuti: | |
| Autori: | MARCO BLANGETTI; ANNAMARIA DEAGOSTINO; HELÈNA ROSSO; CRISTINA PRANDI; CHIARA ZAVATTARO; PAOLO VENTURELLO |
| Data di pubblicazione: | 2007 |
| Abstract: | The treatment of propargylic acetals with various lithium and mixed lithium–potassium Schlosser reagents, has allowed a one-pot synthesis of (E)-1,3-enynes, 1,3-diynes and allenes, depending on the reaction conditions and the selected base. Various reaction conditions were investigated in order to control the selectivity of the reactions and to obtain pure products. The metallation–elimination sequence in the presence of a suitable electrophile has provided a linear route to functionalized (E)-conjugated enynes, diynes and allenes. |
| Editore: | Wiley-VCH Verlag GmBH:PO Box 101161, D 69451 Weinheim Germany:011 49 6201 606147, EMAIL: service@wiley-vch.de, INTERNET: http://www.wiley-vch.de, Fax: 011 49 6201 606328 |
| Volume: | 35 |
| Pagina iniziale: | 5867 |
| Pagina finale: | 5874 |
| Digital Object Identifier (DOI): | 10.1002/ejoc.200700520 |
| Parole Chiave: | Acetals / Superbases / Metalation / Enynes / Diynes |
| Rivista: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
| Appare nelle tipologie: | 03A-Articolo su Rivista |
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|---|---|---|---|---|
| EurJOC2007EniniPrandi.pdf | 2 PDF Editoriale | Utenti riconosciuti Richiedi una copia |
http://hdl.handle.net/2318/26755
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