Lithium and palladium mediated cyclization reactions towards the stereocontrolled synthesis of (hetero)benzo-fused indolizidines
- REBOLLEDO AZKARGORTA, ANE
- Maria Esther Lete Exposito Director
- María Nuria Sotomayor Anduiza Co-director
Defence university: Universidad del País Vasco - Euskal Herriko Unibertsitatea
Fecha de defensa: 18 March 2016
- Francisco Javier Palacios Gambra Chair
- María Luisa Carrillo Fernández Secretary
- Ona Illa Committee member
- Peter Langer Committee member
- Celia Andrés Juan Committee member
Type: Thesis
Abstract
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.