3‐(Methoxycarbonyl)Cyclobutenone as a Reactive Dienophile in Enantioselective Diels–Alder Reactions Catalyzed by Chiral Oxazaborolidinium Ions
Peng Yan, Changxu Zhong, Jie Zhang, Yu Liu, Huayi Fang, Ping Lu
Abstract
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.
Topics & Concepts
Enantioselective synthesisDiels–Alder reactionChemistryBicyclic moleculeDieneCatalysisOctaneBridged compoundsDerivative (finance)BromideOrganic chemistryMedicinal chemistryNatural rubberEconomicsFinancial economicsSynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisTraditional and Medicinal Uses of Annonaceae