The Construction Of Chiral 3-substitued Oxindoles Backbone Catalyzed By The Organic Catalyst And Iridium

The skeleton of 3-substituted oxindoles widely exists in the nature world, not only their biological and pharmacological activities, but also they can be used as multifunctional materials and the important intermediates of organic synthesis. Hence, the development of efficient synthetic method to get chiral 3-substituted oxindole compounds has drawn more and more attention in the fields of natural product chemistry, medicinal chemistry and materials chemistry. We have developed two methods to synthesize the derivatives of 3-substituted oxindoles:the construction of isoquinolin-1(2H)-ones catalyzed by organic catalyst and the 3-allyl-oxindoles initiated by Iridium, which is essential for the development of organic synthetic chemistry.This thesis includes two parts:In the first part, we have developed a novel and efficient method to afford isoquinolin-1(2H)-ones which are ubiquitous units in a number of biologically active compounds with the chiral organic catalyst. We have gained the various functionalized 3-amino-oxindoles obtaining two consecutive quaternary carbon centers. Subsequently, we expanded the range of substrates, and investigated the influence of electrical and other factors on the reactions. Finally, we got the 3-amino-oxindoles with high yields and stereoselectivities. This method will be of wide application in the organic chemistry and medicinal chemistry.In the second part, with iridium and phosphoramidite ligands as the catalysts, 3-substituted-oxindoles have been successfully employed as nucleophiles in the allylation reaction. We have developed the method to synthesize the 3-allyl-oxindoles to construct the core framework of 3-allyl-indoles. Then, we expanded the range of substrates, and investigated the influence of electrical and other factors on the reactions. Finally, we got the 3-allyl-oxindoles with medium yields and general stereoselectivities. With various allylic substrates and oxindoles, this reaction is practical and useful in the terminal alkenes synthesis of nature products and drug analogues.