Gold (I) catalyzed intermolecular cycloadditions of allenes

  1. Ferreira Faustino, Helio Manuel
Dirixida por:
  1. José Luis Mascareñas Cid Director
  2. Fernando José López García Director

Universidade de defensa: Universidade de Santiago de Compostela

Fecha de defensa: 10 de xullo de 2014

Tribunal:
  1. Domingo Domínguez Francisco Presidente
  2. Roberto Sanz Díez Secretario/a
  3. Carlos Alberto Mateus Afonso Vogal
  4. Rosario Fernández Fernández Vogal
  5. José Manuel González Díaz Vogal
Departamento:
  1. Departamento de Química Orgánica

Tipo: Tese

Resumo

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.