Synthesis of bridgehead-azacycles via dual C–N/C–C annulation of α-amino acids, aminals and maleimides

Abstract

The synthesis of various bridged azacyclic adducts has recently become a reemerging topic due to their bioactive and natural product mimic profiles. Accordingly, herein, we report a method for easy access to succinamide-bridged azacyclic derivatives through the metal-free polarization-controlled dual C–N/C–C annulation of readily available α-amino acids, 2-amino benzaldehydes or pyrrole/indole-2-aldehyde and maleimide substrates. This cascade features a rare dipolarophile-induced diastereo-selective amidative annulation, followed by 3 + 2 cycloaddition as key steps.