Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)‐Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides
Seung Cheol Lee, Jeong‐Yu Son, Jin Young Kim, Hyeonsik Eom, Seong Bin Jang, Phil Ho Lee
Abstract
Abstract A regioselective and chemodivergent synthetic approach for azulenolactones and azulenolactams as a new scaffold was demonstrated through Rh(III)‐catalyzed reaction of N ‐methoxyazulene‐1‐carboxamides with sulfoxonium ylides. Sulfoxonium ylides that act as a precursor of secondary carbene was described, leading to the selective formation of azulenolactones and azulenolactams bearing two substituents on a newly introduced double bond. This method demonstrated functionalization of less reactive 2‐position of azulene to overcome the natural reactivity. magnified image
Topics & Concepts
ChemistryRegioselectivityAzuleneRhodiumCarbeneReactivity (psychology)CatalysisSurface modificationCombinatorial chemistryOrganic chemistryMedicineAlternative medicinePhysical chemistryPathologyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSulfur-Based Synthesis Techniques