Chiral Hydroxytetraphenylene–Boron Complex Catalyzed Asymmetric Diels–Alder Cycloaddition of 2′-Hydroxychalcones
Guo-Li Chai, Yan Qiao, Ping Zhang, Rong Guo, Juan Wang, Junbiao Chang
Abstract
(S)-2,15-Cl2-DHTP–boron complex catalyst for the asymmetric Diels–Alder cycloaddition of 2′-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 endo/exo, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions. In addition, a DFT study was performed to explain the stereochemical course of the asymmetric induction.
Topics & Concepts
CycloadditionChemistryCatalysisBoronAsymmetric inductionSubstrate (aquarium)Diels–Alder reactionEnantioselective synthesisCombinatorial chemistryMedicinal chemistryOrganic chemistryStereochemistryGeologyOceanographyOxidative Organic Chemistry ReactionsTraditional and Medicinal Uses of AnnonaceaeAsymmetric Synthesis and Catalysis