Organocatalytic Asymmetric Michael-cyclization Cascade Reaction To Spirocyclicoxindoles Containing Rhodanine Or Thiazolidinediones

Spirocyclic structures have been widely found in a large number of biologically activities and medicinally important compounds. As a subset of spirocyclic compounds, spirocyclicoxindoles have received much attention due to their remarkable biological and medicinal activities. In recent years, although the study of spirocyclic oxindoles have made certain progress, to synthesize some new spirocyclicoxindole compounds is still in high demand.In the first part of the thesis, a catalytic asymmetric Michael-cyclization cascade reaction of 3-isothiocyanato oxindoles and unsaturated rhodanine has been disclosed in the presence of new alkaloid-derived bis-urea catalyst. With the optimized reaction conditions in hand, a series of enantioenriched rhodanine spirooxindole derivatives containing three contiguous chiral centers with two quaternary stereocenters have been synthesized in high yields(up to 99%) with excellent diastereo-(up to >99:1 dr) and enantioselectivities(up to >99% ee), and the absolute configurations of the spirooxindole were assigned by X-ray diffraction analysis.In the second part of the thesis, 3-isothiocyanato oxindoles and thiazolidinediones were used to synthesis thiazolidinedione spirooxindole through a catalytic asymmetric Michael-cyclization cascade reaction by the new alkaloid-derived bis-urea catalyst.