Tesis doctoral de Eider Aranzamendi Uruburu
The research work described in this thesis has focused on the study of enantioselective intra and intermolecular ¿-amidoalkylation reactions catalyzed by chiral brí¸nsted acids for the synthesis of tetrahydroisoquinoline systems. The intermolecular ¿-amidoalkylation reactions of hydroxylactams, generated by parham cyclization of the corresponding imides, with nucleophiles, such as indoles and enamides that have an h bond donor group, catalyzed by sterically demanding binol-derived n-triflylphosphoramides and phosphoric acids, afforded moderate to good enantioselectivities. The reaction is proposed to take place via a bicyclic n-acyliminium /chiral conjugate base ion pair, in which the chiral brí¸nsted acid catalyst may act as a bifunctional catalyst, interacting also with the nucleophile.In a similar way, the enantioselective intramolecular ¿-amidoalkylation reaction requires phenolic activation on the benzene ring acting as internal ¿-nucleophile to achieve reasonable levels of enantioselection. In this case, different substituents can be introduced at c-1 position of the isoquinoline moiety by changing the organometallic reagent at the first step of the organometallic addition/intramolecular ¿-amidoalkylation sequence, giving rise to useful precursors for the construction of more complex alkaloids.
Datos académicos de la tesis doctoral «Chiral bronsted acid catalyzed enantioselective alfa-amidoalkylation reactions in the synthesis of tetrahydroisoquinoline systems«
- Título de la tesis: Chiral bronsted acid catalyzed enantioselective alfa-amidoalkylation reactions in the synthesis of tetrahydroisoquinoline systems
- Autor: Eider Aranzamendi Uruburu
- Universidad: País vasco/euskal herriko unibertsitatea
- Fecha de lectura de la tesis: 19/12/2014
Dirección y tribunal
- Director de la tesis
- Nuria Sotomayor Anduiza
- Tribunal
- Presidente del tribunal: claudio Palomo nicolau
- Juan Antonio Rodríguez (vocal)
- María magdalena Cid fernández (vocal)
- roberto José Sanz díez (vocal)