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Título: | Iron(III)-Promoted Aza-Prins-Cyclization: Direct Synthesis of Six-Membered Azacycles |
Autor: | Carballo, Rubén M.; Ramírez, Miguel A.; Rodríguez, Matías L.; Martín, Víctor S. CSIC ORCID; Padrón, Juan I. CSIC ORCID | Palabras clave: | Hydrocarbons Aldehydes Inorganic compounds Cyclization Ions |
Fecha de publicación: | 26-jul-2006 | Editor: | American Chemical Society | Citación: | Organic Letters 8(17): 3837–3840 (2006) | Resumen: | A new iron(III) halide-promoted aza-Prins cyclization between γ,δ-unsaturated tosylamines and aldehydes provides six-membered azacycles in good to excellent yields. The process is based on the consecutive generation of γ-unsaturated-iminium ion and further nucleophilic attack by the unsaturated carbon−carbon bond. Homoallyl tosylamine leads to trans-2-alkyl-4-halo-1-tosylpiperidine as the major isomer. In addition, the alkyne aza-Prins cyclization between homopropargyl tosylamine and aldehydes gives 2-alkyl-4-halo-1-tosyl-1,2,5,6-tetrahydropyridines as the only cyclic products. | Versión del editor: | https://doi.org/10.1021/ol061448t | URI: | http://hdl.handle.net/10261/212261 | DOI: | 10.1021/ol061448t | ISSN: | 523-7060 | E-ISSN: | 1523-7052 |
Aparece en las colecciones: | (IPNA) Artículos |
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accesoRestringido.pdf | Artículo principal | 16,34 kB | Adobe PDF | Visualizar/Abrir |
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