Lithium and palladium mediated cyclization reactions towards the stereocontrolled synthesis of (hetero)benzo-fused indolizidines

  1. REBOLLEDO AZKARGORTA, ANE
unter der Leitung von:
  1. Maria Esther Lete Exposito Doktorvater/Doktormutter
  2. María Nuria Sotomayor Anduiza Co-Doktorvater/Doktormutter

Universität der Verteidigung: Universidad del País Vasco - Euskal Herriko Unibertsitatea

Fecha de defensa: 18 von März von 2016

Gericht:
  1. Francisco Javier Palacios Gambra Präsident/in
  2. María Luisa Carrillo Fernández Sekretär/in
  3. Ona Illa Vocal
  4. Peter Langer Vocal
  5. Celia Andrés Juan Vocal

Art: Dissertation

Teseo: 443658 DIALNET lock_openADDI editor

Zusammenfassung

The research work described in this thesis is focused on the use of lithium and palladium mediated cyclization reactions for the stereocontrolled synthesis of (hetero)benzo-fused indolizidines through carbon-carbon bond formation. The Parham-type intramolecular carbolithiation via conjugate addition and SN2¿ reactions of aryl and heteroaryllithiums has been investigated for the construction of the indolizidine core present in different type of heterocycles. On the other hand, the competition between Mizoroki-Heck and direct arylation reaction on alkenyl substituted o-halopyridines and o-haloquinolines has been studied. Moreover, a procedure for the generation of tertiary and quaternary stereocenters through Heck cyclization via ß¿-hydride or ß¿-leaving group elimination in different o-halo(hetero)arylmethylpyrroles has been developed.