Diastereoselective Preparation of Silylated Pyrrolidones through Palladium-Catalysed Cyclisations
| Autor: | Serge Thorimbert, Maxime R. Vitale, Max Malacria, Giovanni Poli, Giuliano Giambastiani, Claude Commandeur |
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| Rok vydání: | 2003 |
| Předmět: |
Diastereoselectivity
Silicon Carbon atom Nitrogen heterocycles Organic Chemistry chemistry.chemical_element Ring (chemistry) Medicinal chemistry Tsuji–Trost reaction chemistry.chemical_compound chemistry Moiety Stereoselectivity Physical and Theoretical Chemistry Allylic alkylation Palladium Acetamide |
| Zdroj: | Scopus-Elsevier European journal of organic chemistry (2003): 2702–2708. doi:10.1002/ejoc.200300086 info:cnr-pdr/source/autori:Serge, Thorimbert; Giuliano, Giambastiani; Claude, Commandeur; Maxime, Vitale; Giovanni, Poli; Max, Malacria/titolo:Diastereoselective Preparation of Silylated Pyrrolidones via Palladium-Catalysed Cyclizations/doi:10.1002%2Fejoc.200300086/rivista:European journal of organic chemistry (Print)/anno:2003/pagina_da:2702/pagina_a:2708/intervallo_pagine:2702–2708/volume |
| ISSN: | 1099-0690 1434-193X |
| Popis: | A new palladium-catalysed allylic alkylation affording silylated 3-vinylpyrrolidones has been developed. The method relies upon the interaction between a stabilized acetamide enolate anion and a silicon-containing, nitrogen-tethered η3-allylpalladium moiety. Two variants have been studied, involving the location of the silicon atom on either olefinic carbon atom of the cyclisation precursor. In both cases 5-exo ring closure was the only cyclisation process observed. The stereoselectivity of these processes is discussed. These results contrast with related β-oxo ester cyclisations, in which competitive 7-endo mode is observed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) |
| Databáze: | OpenAIRE |
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