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

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

Universidad de defensa: Universidade de Santiago de Compostela

Fecha de defensa: 21 de julio de 2023

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

Tipo: Tesis

Resumen

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.