Domino Michael/Oxa-Michael Reactions of the Unsymmetric Double Michael Acceptor for Access to Bicyclic Furo[2,3-]pyrrole.

By creating an unsymmetric double Michael acceptor , we were able to synthesize the nonaromatic-fused bicyclic furo[2,3-]pyrrole nucleus using a domino Michael/oxa-Michael reaction. Adopting benzoyl acetonitrile (CN as the electron-withdrawing group) as a substrate, we discovered a (DHQ)AQN-catalyzed method for high diastereo- and enantioselectivity of those products. The reaction path has been determined by isolating the reaction intermediates, and density functional theory calculations support these findings.