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

Angew Chem Int Ed Engl. 2016 Jul 4;55(28):8100-3. doi: 10.1002/anie.201602880. Epub 2016 May 11.

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.

Publication types

  • Research Support, Non-U.S. Gov't