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Cu-Catalyzed Asymmetric Alkenylation of Enone Diesters with Trialkenylboroxines.

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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… Click to show full 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.

Keywords: asymmetric alkenylation; enone; alkenylation enone; enone diesters; diesters trialkenylboroxines; catalyzed asymmetric

Journal Title: Organic letters
Year Published: 2023

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