Highly Atom-Economic and Eco-Compatible Gold(I)-Catalyzed Intramolecular Enantioselective Cyclization Reaction for the Total Synthesis of Saturated Heterocycles

The studies carried out in this thesis deal with the construction of substituted saturated heterocycles, which represent fundamental building blocks in several biologically active molecules, with a particular attention pointed towards the principles of eco-compatibility and atom-economy. This project examines Gold(I)-catalyzed enantioselective heterofunctionalization of allenes performing a complete methodological study to comprehend the mechanistic features of these reactions. Thanks to the results obtained, we developed new chiral ligands in order to achieve a broader substrate applicability and improvements in both yield and stereoselectivity. Furthermore, we explored Gold(I)-catalyzed cyclizations on ene-ynes and monoallylic diols. Both these transformations represent promising tools for the production of different saturated heterocycles, broadening Gold(I)-catalysis applications towards the total synthesis of biologically relevant molecules.