The first highly diastereoselective Michael addition/condensation/Friedel-Crafts alkylation cascade reaction of 3-indolyl-substituted oxindoles with ortho-hydroxychalcones was established, which afforded a wide range of polycyclic indole-bridged chroman spirooxindoles with novel and complex scaffolds in moderate to excellent yields.

A TfOH-catalyzed highly diastereoselective Michael addition/ketalization sequence of 3-hydroxyoxindoles and ortho-hydroxychalcones was developed, leading to biologically important bridged ketal spirooxindoles in moderate to excellent yields. Moreover, some chemical transformations were carried out to further extend the structural complexity and diversity.

A highly diastereoselective multicomponent dearomative multifunctionalization of N-alkyl activated azaarenes with 1,5-diazapentadienium salts has been developed, which not only represented a significant advance in maximum utilization of the reactive sites...