Aminocatalytic functionalization of carbonyl compounds: a powerful strategy for enantioselective reaction development

Identificador:  TDX:1320

Handle: https://hdl.handle.net/20.500.11797/TDX1320

Autors:  Cassani, Carlo

Resum:
In this thesis it is shown how aminocatalysis can be employed to solve different problems in organic synthesis. In a first project three complementary cascade reactions have been optimized for the synthesis of spirocylcic products bearing the benzofuranone moiety. The products were synthetized has single enantiomer exploiting the ability of both primary and secondary aminocatalysts to orthogonally activate ketones and aldehydes. In a second project is reported the first use ofα-substitutedα,β-unsaturated ketonesin aminocatalysisfor developing an asymmetric sulfa-Michael addition reaction. In addition, it was possible to modulate the enforced sense of diastereoselectivity of the catalyst by simply modifying the reaction conditions. Finally we could use, for the first time, chiral secondary amines to promote the dienamine activation of α-branched enals. The catalytic system has been used to realize two enantioselectivetrasformations, a vinylogousaldol and a -alkylation reactions.