Highly Enantioselective Synthesis Of Pyrroloquinolinones And Pyrroloindolones Via N-Heterocyclic Carbene-Catalyzed Domino Reaction

In recent years,the Domino reaction catalyzed by organic small molecule catalyst has been developed rapidly,which has aroused the extensive research interest of chemists.Among them,Nitrogen Heterocyclic Carbene(NHC)has been widely used as a powerful organic catalytic tool in various organic transformations.Because Nitrogen Heterocyclic Carbene can induce a variety of activation modes and different activation modes can be embodied in the same reaction strategy,the domino reaction induced by Nitrogen Heterocyclic Carbene has been developed significantly in the past decade.Among these domino reactions,the most attractive feature is that under mild reaction conditions,complex molecular structures can be rapidly constructed with excellent regioselectivity and stereoselectivity through simple and easily available catalysts,raw materials and simple experimental operations.In the first part of this paper,we will focus on the research progress of the domino reaction in recent years.Pyrroloquinolinones and Pyrroloindolonescompounds are widely used in the fields of chemistry and medicine.The skeleton structure of Pyrroloquinolinones and Pyrroloindolones compounds is common in drug molecules and natural products.Therefore,we have studied the synthesis of Pyrroloindolones and Pyrroloquinolinones by the domino reaction of ?,?-unsaturated aldehydes and imines derived from indolealdehyde.In our reaction strategy,a series of compounds with such structures were synthesized with high yield,excellent regioselectivity and enantioselectivity(yield up to 90% and ee value over 90%).This study provides a new synthesis method and research strategy for the construction of chiral pure Pyrroloindolones and Pyrroloquinolinones derivatives.