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3-(Methoxycarbonyl)cyclobutenone as a Reactive Dienophile in Enantioselective DielsAlder Reactions Catalyzed by Chiral Oxazaborolidinium Ions
Time:2021-03-01       

Cyclobutenone has been used as a highly reactive dienophile in Diels-Alder reactions, however, no enantioselective example has been reported. We disclose herein a chiral oxazaborolidine-aluminum bromide catalyzed enantioselective Diels-Alder reaction of 3-alkoxycarbonyl cyclobutenone with a variety of dienes. Furthermore, a total synthesis of (-)-kingianin F was completed for the first time via enantioenriched cycloadduct bicyclo[4.2.0]octane derivative.

   https://onlinelibrary.wiley.com/doi/10.1002/anie.202014308