Gold (I) catalyzed intermolecular cycloadditions of allenes

• Autores: Helio Manuel Ferreira Faustino
• Directores de la Tesis: José Luis Mascareñas Cid (dir. tes.), Fernando José López García (codir. tes.)
• Lectura: En la Universidade de Santiago de Compostela ( España ) en 2014
• Idioma: inglés
• Tribunal Calificador de la Tesis: Domingo Domínguez Francisco (presid.), Roberto Sanz Díez (secret.), Rosario Fernández Fernández (voc.), José Manuel González Díaz (voc.), Carlos Alberto Mateus Afonso (voc.)
• Materias:
  • Química
    • Química orgánica
      • Química de carboaniones
      • Química de carbonio
      • Compuestos organometálicos
• Enlaces
  • Tesis en acceso abierto en: MINERVA
• Resumen

  • We describe our efforts in the development of intermolecular Au-catalyzed cycloadditions with allenic scaffolds. In particular, we demonstrate that the use of allenamides, a particularly accessible and versatile type of allenic scaffold, allowed the discovery of highly selective and even enantioselective gold-catalyzed (4 + 2) cycloadditions to 1,3-dienes.

    We also pursue the development of a gold-catalyzed intermolecular (2 + 2) cycloaddition, which could be eventually achieved using appropriate alkenes and a phosphite-gold catalyst.

    Finally, a simple and highly versatile cascade cycloaddition between allenamides and carbonyl-tethered alkenes, including several enantioselective examples, is also described. This method enables a straightforward and highly efficient entry to oxa-bridged seven-, eight- and even nine-membered rings.