Cu-Catalyzed Asymmetric Alkenylation of Enone Diesters with Trialkenylboroxines

The Cu-catalyzed asymmetric conjugate addition of trialkenylboroxines to enone diesters is reported. This operationally simple and scalable reaction proceeded at room temperature, and a wide range of enone diesters and boroxines were tolerated under the applied reaction conditions. The practical utility of this approach was demonstrated via the formal synthesis of (+)-methylenolactocin. Mechanistic studies revealed that two different catalytic species work synergistically in the reaction.

Automated summary

The Cu-catalyzed asymmetric conjugate addition of trialkenylboroxines to enone diesters is described. This operationally simple and scalable reaction proceeds at room temperature and tolerates a wide range of substrates. The practical utility of this method is demonstrated through the formal synthesis of (+)-methylenolactocin. Mechanistic studies reveal the synergistic action of two different catalytic species.