Asymmetric Organocatalytic Synthesis Of Spirooxindoles And Piperazine-indole Derivatives

This thesis mainly includes the following three parts:Cycloaddition reaction, a reaction in synthetic organic chemistry, is an important way to build a ring system. It has been concerned widely for a long time. In the past ten years, with the rapid development of asymmetric organocatalytic, organocatalytic asymmetric cycloaddition reaction has become a hot research topic. Organocatalytic reaction has the advantages of mild reaction condition, simple operation and excellent stereoselectivity. Especially, the organocatalytic cycloaddition construction of heterocyclic compounds showed more simple and efficient role. Therefore, the development of new organocatalytic asymmetric cycloaddition reaction has become an effective means to construct various important and complex ring system. This chapter summarizes the progress of organocatalytic asymmetric cycloaddition reactions.The enantioselective construction of a spirocyclic quaternary stereogenic carbon center at the C2 position of indole has long been an elusive problem in organic synthesis. Herein, by employing a rationally designed hydrogen-bonding network activation strategy, for the first time, 2,2’-pyrrolidinyl-spirooxindole which is a valuable and prevalent indole alkaloid scaffold was directly obtained through catalytic asymmetric [3 + 2] cycloaddition reaction with high yields and excellent stereoselectivities.Piperazino-indoles are widely present in various natural products and drug molecules, and the development of a simple and effective method of synthesis is very meaningful. Based on our previous efforts on the synthesis of indole compounds and interest in organocatalytic transformations, we plan to realize the synthesis of piperazine-indole derivatives at high yield by using the secondary amine catalytic mode. However, we have not realized the reaction of "one-pot" and made the enantioselective well-controlled.