Chiral Phosphoric Acid Catalyzed N-Alkylation Of Indoles And Dearomatization Of Isoquinolines

This thesis mainly focuses on the application of catalytic asymmetric dearomatization(CADA)reaction in the construction of highly functionalized polycyclic compounds.With chiral phosphoric acid as catalyst,catalytic asymmetric dearomatization reaction of isoquinolines and N-alkylation of indoles was realized.A series of compounds containing dearomatized molecular fragments of 1,2-dihydroisoquinoline and N-alkylated derivatives of indole were constructed successfully in good yields and enantioselectivities at room temperature(up to 98%yield,94%ee),providing a strategy for the asymmetric synthesis of this kind of novel skelecton.Indoles and dihydroisoquinoline exsit widely in alkaloids,both of which possess abundant physiological and pharmacological activities.Therefore,the success of this methodology development provided the possibility to explore more diverse molecules with potential biological activity.This method features mild reaction conditions,easy operation,readily available starting materials,and broad substrate scope.The compatibility of the gram-scale reaction and diverse transformations of the products further demonstrated the potential utility of this method.In addition,due to the tedious synthesis and difficult recovery of chiral phosphoric acid,three kinds of organic porous materials based on it were synthesized.We found the materials possess catalytic activities and can be recycled after filtration,with the yield and enantioselectivity of the product remaining unchanged.The synthesis of these materials is expected to realize the immobilization of chiral phosphoric acid,thus reducing the cost of synthesis.