Lithium and palladium mediated cyclization reactions towards the stereocontrolled synthesis of (hetero)benzo-fused indolizidines
- REBOLLEDO AZKARGORTA, ANE
- Maria Esther Lete Exposito Director/a
- María Nuria Sotomayor Anduiza Codirector/a
Universitat de defensa: Universidad del País Vasco - Euskal Herriko Unibertsitatea
Fecha de defensa: 18 de de març de 2016
- Francisco Javier Palacios Gambra President/a
- María Luisa Carrillo Fernández Secretari/ària
- Ona Illa Vocal
- Peter Langer Vocal
- Celia Andrés Juan Vocal
Tipus: Tesi
Resum
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.