Silver-Catalyzed Synthesis Of Azide/Nitrating Oxindoles And Palladium-Catalyzed Enantioselective Synthesis Of α-Amino Acids Esters Derivatives

3,3-Disubstituted oxindoles are an important heterocyclic compounds, and have been widely used in natural product and pharmaceuticals. We provided a simple and efficient strategy for synthisis of a series of oxindole compounds, which based on difunctionalization of N-methyl-N-phenylacrylamide. In this thesis, we first used silver-catalyzed radical reaction process to synthesize azido and nitro oxindoles respectively which was applied to the systhesis of a number of oxindole alkaloids.Chiral α-amino acids derivatives are a kind of useful compounds which are widely used as the buildingblock for cores of peptides, proteins, and pharmaceutical agents These amino acids also have been used in organic chemistry to synthesize natural products, chiral catalysts, and ligands. The main methods previously reported to synthesize chiral amino acid derivatives were the nucleophiles addition to imines. In this thesis, we first combined C-H bond oxidation and palladium-catalyzed asymmetric addition to imine strategies to accomplish the synthesis of a series of chiral a-amino acid ester derivatives.This thesis was composed of four chapters according to the research content:Chapter 1. We summrized the methodologies which have been developed for the synthesis of diversely functionalized 3,3-disubstituted oxindoles through difunctionalization of arylacrylamides over past decades.Chapter 2. A novel and inexpensive method of non-toxic, silver-salt catalyzed carboazidation of arylacrylamides to afford corresponding azide oxindoles had been reported. This reaction system exhibited great functional group tolerance.Chapter 3. A silver-catalyzed carbonitration of alkenes involving concomitant direct C-H functionalization and C-N bond formation to synthesize nitrating oxindoles had been developed. Starting from our product, CR TH2 receptor antagonist skeleton can be obtained with further modification.Chapter 4. A novel pattern for the synthesis of a series of chiral a-amino acid derivatives by palladium-catalyzed enantioselective direct C-H oxidation and arylation reaction had been developed. This method showed significant promise for a potential pathway of enantioselective Csp3-C bond formations by direct C-H oxidative.