Rhodium-Catalyzed Desymmetric Arylation of <i>γ,γ</i>-Disubsituted Cyclohexadienones: Asymmetric Synthesis of Chiral All-Carbon Quaternary Centers
Yu Qiao, Shiming Bai, Xiaofeng Wu, Ying Yang, He Meng, Jialin Ming
Abstract
The desymmetric arylation of prochiral cyclohexadienones with ArZnCl in the presence of an (R)-segphos–rhodium catalyst gave high yields of the corresponding cyclohexenones, which contain a chiral arylated carbon center at the β-position and a chiral all-carbon quaternary center at the γ-position, with high diastereo- and enantioselectivities. This catalytic system was also applied to the arylation of spirocarbocyclic cyclohexadienones and afforded the corresponding cyclohexenones bearing a chiral spiro quaternary carbon with high dr and ee.
Topics & Concepts
ChemistryRhodiumQuaternary carbonCatalysisCarbon fibersAsymmetric carbonMedicinal chemistryOrganic chemistryEnantioselective synthesisOptically activeComposite numberComposite materialMaterials scienceAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods