Enantioselective Assembly of Aza-Heterocycles through Pd(II)-Catalyzed Annulations Initiated by the Activation of C‒H Bonds

  1. González González, José Manuel
Dirixida por:
  1. José Luis Mascareñas Cid Director
  2. Moisés Gulias Costa Director

Universidade de defensa: Universidade de Santiago de Compostela

Fecha de defensa: 21 de xullo de 2023

  1. Félix Rodríguez Iglesias Presidente/a
  2. Manuel Nappi Secretario
  3. Allegra Franchino Vogal
  1. Departamento de Química Orgánica

Tipo: Tese


In this PhD thesis, we described our efforts towards the development of a series of enantioselective Pd(II)-catalyzed formal cycloadditions initiated by the activation of C–H bonds, using allenes as cycloaddition partners. These transformations allowed the asymmetric assembly of highly valuable aza- heterocyclic structures in a straightforward and sustainable manner through the activation of either C(sp²)−H or C(sp³)−H bonds. On the one hand, we have discovered a kinetic resolution of allylamine derivatives based on a (4+2) annulation, providing an efficient entry to enantioenriched tetrahydropyridines. On the other hand, we have designed and developed acetylated versions of NOBIN (NOBINAc) as new chiral ligands, which have allowed the asymmetric assembly of 3- and 2-benzazepine skeletons through (5+2) annulations.