Small Molecule Activation for the Formation of Heterocyclic Compounds

Identificador:  TDX:2659

Handle: https://hdl.handle.net/20.500.11797/TDX2659

Autors:  Laserna Ayora, Victor

Resum:
This thesis focuses on the activity of aluminium aminotriphenolates in the activation of epoxides and their couplings to other molecules in the formation of a series of heterocycles. The catalyst is a Lewis Acid which interacts with the epoxide enhancing its electrophilicity, favoring ring opening processes and couplings to heterocumulenes such as CO2 or SO2. We describe methodologies for the synthesis of oxazolidinones, carbamates, cyclic sulfites or cyclic carbonates. Many of these processes had already been described for other catalyst systems, but we have focused on the less reactive cyclic epoxides, whose products are more interesting as they have similarities to many natural products. Studying the different reaction mechanisms related to these reactions and changing the components and conditions of our catalytic system we have achieved complete stereoselectivity in our reactions and even in some cases stereodivergence.