Synthesis and application of silylated pyrrolidines : enantioselective organocatalytic synthesis of alpha-trifluoromethyl alpha-amino acid derivatives and copper catalyzed multicomponent reactions

TL;DRAbstract

The work presented in this thesis focuses on the synthesis and application of silylated pyrrolidines, chiral phosphoric acid catalyzed Friedel-Crafts reactions to form quaternary trifluoromethylated amino acid derivatives and copper-catalyzed four-component reactions towards functionalized imidates. First, various silylated pyrrolidines were obtained in high yields by asymmetric synthesis. Enantiopure (S)-2-(diphenylmethylsilyl)pyrrolidine was furnished after recrystallization of its HCl salt and the absolute configuration was confirmed by X-ray crystal structure analysis. The application of these Lewis base structures, bearing a silyl group directly attached to the pyrrolidine, in asymmetric Michael-type addition reactions has been demonstrated. The catalyzed enantioselective addition of propanal and butanal to nitroolefins resulted in the desired nitro aldehydes in high yields (up to 99%), diastereoselectivities (up to 97:3 dr) and enantioselectivities (up to 95.5:4.5 er). The second

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