Catalytic Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines

Abstract

Reported herein is a bifunctional-organocatalyst-mediated enantioselective inverse-electron-demand 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with azlactones. The strategy provides concise access to enantioenriched C1-substituted tetrahydroisoquinolines featuring a pyrazolidinone scaffold. Moreover, the scalability and practical utility of this protocol was well demonstrated by employing a gram-scale reaction and some representative transformations.

Keywords: cycloaddition; hydrogen bonds; lactones; organocatalysis; synthetic methods.