Three-Component, Diastereoselective [6 + 3] Annulation of Tropone, Imino Esters, and Arynes

Abstract

A transition-metal-free, three-component, and diastereoselective [6 + 3] annulation reaction employing tropone, imino esters, and arynes allowing the synthesis of bridged azabicyclo[4.3.1]decadienes is demonstrated. The key nitrogen ylides for the [6 + 3] annulation were generated by the addition of imino esters to the arynes followed by a proton transfer. The nitrogen ylides undergo a regioselective addition to tropone to furnish the desired products in moderate to good yields with good functional group tolerance under mild conditions.