BETA-AMINO ACIDS AS TOOL FOR THE PREPARATION OF FOLDAMERS AND NANOMATERIALS

beta-Amino acids are analogues of alpha-amino acids (AAs) in which the amino group is linked to the beta-carbon instead of the alpha-carbon. In this thesis are reported different approces to beta amino acids both from the synthetic and applicative points of view. Beta-2,3-diaryl-beta amino acids: Development of diastero- and enantioselective synthesis of variously substituted 2,3-Diaryl amino esters using a TiCl4 catalyzed Mannich-like reation. Preparation of -Hybrid peptides containing 2,3-Diaryl amino acids and Alanine. Structural characterization of -hybrid using NMR analysis and X-Ray diffraction to understand if their strong aromatic component affect the secondary structure of these peptide. Studies on the self assembly of these derivatives in order to obtain sopramolecular architectures. Tetrahydroisoquinoline-4-carboxylic acid (TIC): Development of a simple and scalable synthesis of tetrahydroisoquinoline 4-carboxylic acid, solving the problems encountered using the literature synthetic protocol. Bio-enzymatic resolution of TIC. Preparation of model peptides in in order to study TIC conformational behavior. Rhodium catalyzed transformation of diazobarbonyl-piperidine derived from beta amino acids n efficient preparation of three different classes of -diazocarbonylpiperidine compounds derived from -AAs, including the simple Nipecotic acid, its benzocondensate, i.e. TIC, and TIC derivatives in which a further aryl moiety is present at position 3. Generation of rhodium carbenes starting from diazocarbonyl derivatives and rhodium-(II) dimer catalysts to give intramolecular carbene insertion.Search of the best catalyst and the optimal reaction conditions to drive the chemoselectivity of the insertion reaction. NMR characterization of the polycyclic compounds obtained by intramolecular carbene insertions.