A Highly Diastereoselective Three-component Tandem Michael Addition/Cyclization Reaction To Multisubstituted Pyrrolidines And The Study Of InBr₃Catalyzed Three-component Reactions

Multi-component reactions (MCRs) and cascade reactions have received great attention because they have advantages of highly efficient synthetic strategies, atom economy, convergence, flexibility and rapid construction of diverse and complex molecules. Recently, our group have reported various types of carbenoid-initiated three-component reaction. But narrow substrate scope is an obvious disadvantage in most reactions, meanwhile, the expensive Rh2(OAc)4restricts some application of these reactions to some extent, and relative cheap catalysts are highly desirable.In this thesis, a highly diastereoselective three-component tandem Michael addition/cyclization reaction of diazoacetophenones with anilines and unsaturated ketoesters was developed, which provides general, easy and highly efficient access to multisubstituted pyrrolidines in good yield with high diastereoselectivity.Considering the expensive Rh2(OAc)4is often used in three-component reaction as catalyst, we screened other catalyst to reduce cost. To our delight, we found InBr3promoted three-component reaction of an aryldiazoacetate, an alcohol, and an electron deficient carbonyl compound to give a,(3-dihydroxyl acid derivatives in good yield with high diastereoselectivity.