Silver-Catalyzed Asymmetric Desymmetrization of Cyclohexadienones via Van Leusen Pyrrole Synthesis
Mohamed Ahmed Abozeid, Hun Young Kim, Kyungsoo Oh
Abstract
A catalytic asymmetric desymmetrization of cyclohexadienones was accomplished via Van Leusen pyrrole synthesis in the presence of a chiral silver catalyst. The ready access to chiral-fused pyrrole derivatives is attributed to the identification of a suitable isocyanomethyl sulfone surrogate, NasMIC. The current Ag(I)–chiral phosphino-carboamide ligand system can be extended to the kinetic resolution of racemic cyclohexadienones, capitalizing on the differentiated reactivity of chiral quaternary complexes from AgSbF6, chiral ligand (L*), cyclohexadienone, and NasMIC.
Topics & Concepts
DesymmetrizationChemistryPyrroleKinetic resolutionCatalysisEnantioselective synthesisLigand (biochemistry)Reactivity (psychology)StereochemistryCombinatorial chemistryOrganic chemistryMedicineAlternative medicinePathologyReceptorBiochemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods