Grygorenko O. Conformationally constrained and rigid proline analogues

The thesis is devoted to the synthesis of conformationally constrained and rigid proline analogues, their derivatives and investigation of their conformational behavior. Three novel conformationally constrained and rigid proline analogues were synthesized. A novel reagent for the synthesis of 2-cyanopyrrolidines - (phenylethylamino)isobutyronitrile - was proposed. The limitation scope of its reaction with halocarbonyl compounds was studied. Model N-acetyl-N'-methylamide derivatives of the obtained proline analogues were synthesized. It was shown that their conformational behavior is similar to that of prolind derivatives. Novel conformationally constrained piperazinones - hexahydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives - were synthesized. Novel rigid analogues of CBS catalysts were synthesized from camphor. It was found that their catalytic activity towards enantioselective reduction of ketones by borane complexes is low.