Anion-Relay Double Aza-Michael–Michael Cascades to Enone-Tethered Cyclohexadienones: Access to an Intricate Bridged Ring System

Abstract

An anion-relay double aza-Michael−Michael addition strategy has been reported for the synthesis of intricate scaffolds from enone-tethered cyclohexadienones and primary amines. This method discloses the base-catalyzed synthesis of highly valued bridged aza-tricyclic frameworks with a high level of product selectivity and stereoselectivity. Gram scale synthesis and synthetic transformation were shown to afford structurally diverse bridged aza-polycyclic amines. Control experiments and the kinetic profile were studied to determine a plausible reaction mechanism.