Development of new asymmetric organocatalytic domino reactions for the synthesis of (benzo-fused) five- and benzo-fused six-membered cyclic compounds

The present dissertation reports the work performed in the field of organocatalyzed domino reactions. The work can be divided into four projects. The first project included the development of a Michael/Michael domino reaction for the construction of polysubstituted 1,2,3,4-tetrahydronaphthalenes through the reaction between 2-(nitromethyl)nitrostyrene and α,β-unsaturated aldehydes successfully promoted by TMS-protected diphenylprolinol. In the second project a new asymmetric organocatalyzed domino reaction for the construction of 4,5-disubstituted 3-hydroxy-1H-pyrrol-2(5H)-ones was developed. The Brønsted base cupreine successfully facilitated the Mannich/cyclization cascade sequence between α-ketoesters and aldimines. Next, the reaction between the o-divinylketone and 3-phenylpropanal in conditions of secondary amine organocatalysis was investigated. In the last project, an enantioselective organocatalytic Friedel-Crafts-type Michael addition of electron-rich arenes to nitroolefins was studied