Cu-Catalyzed Asymmetric Alkenylation of Enone Diesters with Trialkenylboroxines.

Abstract

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.