Synthesis and consecutive reactions of α-aminocyclobutanone derivatives

The thesis deals with the development and the application of new synthetic methodologies in organic chemistry. The first part describes an organocatalytic enantioselective synthesis of α-(benzylamino) cyclobutanones by employing a tandem condensation/intramolecular rearrangement/proton transfer reaction and starting from α-hydroxycyclobutanone and a selection of benzylamines. In the second part, a practical method for the synthesis of optically active cyclobutanones α-aminoacid esters is presented, via an organocatalytic asymmetric condensation reaction between racemic α-hydroxycyclobutanone and chiral N-alkyl-α-amino ester derivatives. Therefore, an original synthetic protocol for the preparation of highly functionalized tryptamines from α-hydroxycyclobutanone and secondary arylamines via a solvent-free Brønsted acid catalysed two-step reaction sequence is reported in the third part. Finally, the last part covers the synthesis of novel bicyclic oxetanes though Paternò-Büchi reaction and their preliminary evaluation as intermediates for post-functionalization reactions.The thesis deals with the development and the application of new synthetic methodologies in organic chemistry. The first part describes an organocatalytic enantioselective synthesis of α-(benzylamino) cyclobutanones by employing a tandem condensation/intramolecular rearrangement/proton transfer reaction and starting from α-hydroxycyclobutanone and a selection of benzylamines. In the second part, a practical method for the synthesis of optically active cyclobutanones α-aminoacid esters is presented, via an organocatalytic asymmetric condensation reaction between racemic α-hydroxycyclobutanone and chiral N-alkyl-α-amino ester derivatives. Therefore, an original synthetic protocol for the preparation of highly functionalized tryptamines from α-hydroxycyclobutanone and secondary arylamines via a solvent-free Brønsted acid catalysed two-step reaction sequence is reported in the third part. Finally, the last part covers the synthesis of novel bicyclic oxetanes though Paternò-Büchi reaction and their preliminary evaluation as intermediates for post-functionalization reactions