Novel Enantioselective Aminocatalytic Processes by means of Vinylogous Reactivity and Photoredox Catalysis

Identifier:  TDX:2970

Handle: https://hdl.handle.net/20.500.11797/TDX2970

Authors:  Bastida Borrell, David

Abstract:
In the present thesis it is shown how aminocatalysis may be used to solve some problems for synthetic organic chemists'. Combination of aminocatalysis with the concept of vinylogy is the key concept for the enantioselective functionalization of remote positions of carbonyl compounds. In the first project a bifunctional primary amine-thiourea catalyst that can combine H-bond-directing activation of the electrophile with the dienamine activation for an asymmetric vinylogous aldol reaction. In the second project, using a chiral secondary amine we expanded the potential of organocascade catalysis by including vinylogous reactivity functionalizing exclusive δ poitions. In the last project, we developed an enantioselective radical conjugate addition of enones by trapping photochemically generated carbon-centered radicals using iminium ion activation generated in-situ by condensation of primary amines with enones.