Asymmetric Catalytic Michael-cyclization Tandem Reaction Access To N-heterocyclic Spirocyclicoxindoles

N-heterocyclic spirooxindoles,with attractive and special skeletons,have been widely found in biologically active compounds and drug molecules.As key intermediates for preparation of drug,spirooxindoles have become attractive synthesis targets and attracted more and more attention.In recent years,although the research of N-heterocyclic Spirooxindoles have made some progress,there are still great demands for the development of some new spirooxindoles with diversified structures.In the first part of the thesis,a Michael-cyclization tandem reaction of3-acylaminooxindoles and ?,?-unsaturated-?-ketoesters was performed to synthesize3,3'-azacyclic spirooxindoles in the presence of an organic catalyst.Under the optimized reaction conditions,the scope of this reaction was investigated,and a series of N-heterocyclic spirooxindole derivatives were obtained with multiple chiral centers and excellent dr(up to >95:5 dr)and ee(up to >98% ee).In the second part of the thesis,a Michael-cyclization tandem reaction of3-aminooxindoles and chalcone was performed to synthesize 3,2'-azacyclic spirooxindoles in the presence of an organic catalyst.Under the optimized reaction conditions,the scope of this reaction was investigated,a series of N-heterocyclic spirooxindole derivatives were obtained with multiple chiral centers and excellent dr(up to >95:5 dr)and medium ee(up to 82%ee).