Application of Indolyl Ynones in the Construction of Chiral Carbazoles and Pyrroloindolines by Organo and Metal Sequential Catalysis

Abstract

The enantioselective synthesis of carbazoles and pyrroloindolines has been achieved through organo-catalyzed and metal sequential-catalyzed one-pot reactions of indolyl ynones. Chiral carbazoles can be synthesized from the reactions of indolyl ynones and nitroolefins through an organo-catalyzed Michael addition followed by a gold-catalyzed Friedel-Crafts reaction/aromatization process. The reactions of indolyl ynones and N-tosyl imines lead to the generation of pyrroloindolines via an organo-catalyzed Mannich reaction and a silver-catalyzed dearomatizing spirocyclization/N,N-acetalization cascade reaction.