Leveraging catalysis versatility towards innovative methodologies in organic synthesis

The demand for complex chiral molecules necessitates the development of efficient and sustainable synthetic methodologies. Our approach aligns with Green Chemistry principles by leveraging asymmetric catalysis—a Nobel Prize-recognized tool for enantioselective synthesis—and multicomponent reactions (MCRs), which maximize synthetic efficiency by minimizing steps and waste. This thesis presents six distinct research projects conducted over three years, with a central focus on catalytic methodology development. First, key efforts included the exploitation of fully renewable alginate gel beads to transfer chirality from a biopolymer scaffold, successfully achieving asymmetric nucleophilic addition of indoles to nitrostyrenes. Then, significant work was dedicated to developing novel MCRs utilizing stabilized sulfoxonium ylides. This led to the successful implementation of an enantioselective 3CR (sulfoxonium ylides, benzaldehydes, and thiophenols), which provided critical mechanistic insights. Subsequent efforts yielded highly diastereoselective 4CR and 3CR pathways for synthesizing valuable α-sulfanyl-β-amino acid derivatives and phthalide core scaffolds. Finally, a project carried out during the research period abroad explored metal-free radical coupling of diazonium salts with Eschenmoser-like salts, an intriguing and novel proof of concept for metal-free radical couplings. Collectively, this research demonstrates a commitment to advancing efficient, catalytic, and waste-reducing synthetic strategies for added value molecules.