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

  1. Bernabeu, M.C. 1
  2. Chinchilla, R. 1
  3. Nájera, C. 1
  4. Rodríguez, M.A. 2
  1. 1 Universitat d'Alacant
    info

    Universitat d'Alacant

    Alicante, España

    ROR https://ror.org/05t8bcz72

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron Letters

ISSN: 0040-4039

Año de publicación: 1996

Volumen: 37

Número: 20

Páginas: 3595-3598

Tipo: Artículo

DOI: 10.1016/0040-4039(96)00631-4 SCOPUS: 2-s2.0-0029884132 WoS: WOS:A1996UL79200051 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron Letters

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Resumen

(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.