Manuel Nappi, PhD student under the supervision of Prof. Paolo Melchiorre, has defended his PhD Thesis entitled “Novel Aminocatalytic and Photochemical Reactions” (assigned to the Organic and Analytical Chemistry Department of the Universitat Rovira i Virgili) publicly on October 16th at the ICIQ auditorium.
The members of his evaluation committee were: Prof. Antonio M. Echavarren (ICIQ), Prof. Miquel Costas (Universitat de Girona) and Prof. David MacMillan (Princetown University).
The PhD dissertation relied on the development of new, operationally simple synthetic reactions using aminocatalysis, photochemistry and their combination. Asymmetric aminocatalysis has allowed to develop the elusive catalytic asymmetric Diels-Alder reaction of in situ generated ortho-quinodimethane intermediates. Further studies on the indole-2,3-quinodimethane strategy allowed the development of a multicatalytic one-pot Diels-Alder/benzoin reaction sequence and an asymmetric aza-Michael reaction. In a six months research period in Princeton, the direct β-aldol reaction has been achieved via the synergistic combination of photoredox catalysis and organocatalysis. Finally, an operationally simple protocol for the direct aromatic perfluoroalkylation of α-cyano arylacetates has been developed using visible light-EDA complex activation.