Supramolecular Scaffolds for Biomimetic Catalysis

This PhD thesis is concerned with the design, synthesis and the characterization of supramolecular scaffolds for biomimetic catalysis. Development of new organocatalytic systems based upon well-designed calix[4]arene derivatives was made and their application for on water catalysis of the Vinylogous Mukaiyama Aldol Reaction (VMAR) was explored. The obtained results showed that combination of high hydrophobicity and synthetic versatility of calixarene macrocycles can be exploited for a kind of catalysis which permits the use of mild conditions and the choice of a reaction medium, water, different from organic solvents which are largely employed for the synthesis of fine chemicals and are responsible of large energy usage and industrial pollution4. So, calixarene macrocycles can be exploited to develop new environmentally oriented catalytic approaches. The target molecules bear a butenolide moiety substituted at γ position; this moiety represents a recurring motif in several compounds displaying a wide range of biological activities5. Moreover, thanks to the presence of functional groups typically involved in processes of molecular recognition through weak interactions, like hydroxyl and carbonyl functionalities, these products exhibit interesting features in their solid state assembly, showing that playing on non covalent interactions could be a good opportunity to build supramolecular architectures resembling the natural ones... [edited by Author]