Synthesis Of Five - Membered Cyclic Compounds By Organic Phosphine - Catalyzed Domino Reaction

Phosphine catalyzed domino reaction was developed recently and can build several chemical bonds in one process, such as C-C, C-N, C-O, C-S, with high selectivity and wide substrate scope. So this strategy plays an important role for the construction of five membered cyclic compounds. This paper is composed of three parts:In the first chapter, we will make an overview of phosphine catalyzed Domino reaction, and its application in the preparation of five-membered carbocyclic compounds, heterocyclic compounds containing nitrogen, oxygen, sulfur, and in the process of organic total synthesis.In the second chapter, we use the conjugated dienes as C3synthon reacting with2-substituted1,1-dicyanoalkene to constructing cyclopentene with high yield and high chemo-and diastereoselectivity. More importantly, the major trans-isomer products are complementary to Lu’s [3+2] cycloaddition. This type of transformation has the advantages of high atom economy, high process economy, easily prepared, wild condition and provides a new method for the synthesis of cyclopentene skeletons.In the third chapter, we have realized a Domino reaction between methyleneindolinones and conjugated dienes for the synthesis of carbocyclic spirooxindoles. In the reaction, two new C-C bonds together with a quaternary carbon center were formed. This study is the further investigation of phosphine catalyzed Domino reaction for the construction of bicyclic skeletons and monocyclic skeletons.