Assessing the versatility of organocatalysis as a strategy for enabling novel asymmetric transformations

Identificador:  TDX:1432

Handle: https://hdl.handle.net/20.500.11797/TDX1432

Autors:  Bergonzini, Giulia

Resum:
In a first project, we developed the direct asymmetric -alkylation of -branched enals exploiting the compatibility between dienamine activation and Brønsted acid catalysis. In a subsequent study, the mild conditions provided by organocatalysis allowed for the use of dioxindole and its analogues to access valuable enantioenriched chiral 3-hydroxyoxindoles. Moreover, the versatility of organocatalysis enabled the unprecedented employment of anion-binding catalysis to control the reactivity of a photoredox-generated ion-pair intermediate as a new methodology for the enantioselective oxidative Mannich-type functionalization of tetrahydroisoquinolines. Finally we found that the photochemical activity of electron donor-acceptor (EDA) complexes, generated between electron-poor benzylic substrates and perfluorohexyl iodide, enables the direct perfluoro-alkylation of arenes driven by visible light.