Organic Catalyzed Michael Addition Reaction And Cui / Amino Acid Catalytic System In The Synthesis Of Polysubstituted Furan Compounds Applied Research

China Book Classification No.:062In the first part of this dissertation, we have developed a highly efficient domino process for the assembly of polysubstituted piperidines and tetrahydropyrans. This process allows for the formation of four contiguous stereocenters in the piperidine or tetrahydropyran ring in one step with excellent enantioselectivity. The diverse functional groups in the products will permit furthermanipulation for synthesizing bioactive compounds. More importantly, our results demonstrated that some trisubstituted nitroolefins are suitable Michael acceptors for organocatalytic reactions, in which the intramolecular hydrogen bond might play an important role for activating the nitro group.In the second part of this dissertation, we have developed a new diastereo-and enantioselective organocatalytic cascade double Michael reaction in which four or five stereogenic centers were controlled. It enables the facile assembly of tetrasubstituted chiral cyclohexane from simple achiral molecules in a single operation. In addition, the products could be transformed into more valuable building blocks.In the third part of this dissertation, we have developed a new and convenient method to assemble polysubstituted furans from vinyl iodides and terminal alkynes, which involves a copper/L-proline-catalyzed cross-coupling and additive cyclization process. Our result gives an additional example for synthesis of heterocycles via ligand-promoted Ullmann-type coupling reaction. Compared with previous stepwise methods, our approach has the advantages of simple operation and inexpensive catalysts. The generality of this method has been demonstrated by preparing a wide range of substituted furans. These features would make this method an attractive choice for furan synthesis.