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(2E)-4-Methoxy-2,4-pentadienamides as New Dienes in the Diels-Alder Reaction

Identificadores del recurso

https://investigacion.unirioja.es/documentos/5bbc68e2b750603269e81147

info:doi:10.1016/0040-4039(96)00631-4

urn:issn:0040-4039

Procedencia

(Repositorio Institucional de la Universidad de La Rioja (RIUR))

Ficha

Título:: (2E)-4-Methoxy-2,4-pentadienamides as New Dienes in the Diels-Alder Reaction
Descripción:: (2E)-4-Methoxy-2,4-pentadienamides have been stereoselectively prepared by treatment of (2E,4E)-5-tosyl-2,4-pentadienamides with 1M methanolic potassium hydroxide in good yields. They behave as new electron-rich dienes in Diels-Alder reactions to give stereoselectively highly functionalized adducts 3 mainly with endo-selectivity and, after hydrolysis, only their corresponding cyclohexanone derivatives 4. Semi-empirical calculations corroborate their reactivity.
Idioma:: English
Relación:: info:eu-repo/semantics/altIdentifier/doi/10.1016/0040-4039(96)00631-4; info:eu-repo/semantics/altIdentifier/wos/WOS:A1996UL79200051; info:eu-repo/semantics/altIdentifier/pissn/0040-4039; (2E)-4-Methoxy-2,4-pentadienamides as New Dienes in the Diels-Alder Reaction, 1996, vol. 37, núm. 20, pág. 3595-3598
Autor/Productor:: Bernabeu, M.C.; Chinchilla, R.; Nájera, C.; Rodríguez, M.A.
Derechos:: info:eu-repo/semantics/openAccess
Fecha:: 1996
Tipo de recurso:: info:eu-repo/semantics/article; Subtype: Article; info:eu-repo/semantics/publishedVersion
Formato:: application/pdf

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3. <dc:creator>Chinchilla, R.</dc:creator>
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5. <dc:creator>Rodríguez, M.A.</dc:creator>
6. <dc:description>(2E)-4-Methoxy-2,4-pentadienamides have been stereoselectively prepared by treatment of (2E,4E)-5-tosyl-2,4-pentadienamides with 1M methanolic potassium hydroxide in good yields. They behave as new electron-rich dienes in Diels-Alder reactions to give stereoselectively highly functionalized adducts 3 mainly with endo-selectivity and, after hydrolysis, only their corresponding cyclohexanone derivatives 4. Semi-empirical calculations corroborate their reactivity.</dc:description>
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