Maleimide‐Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones <i>via</i> Rh(III)‐Catalyzed C−H Activation of Sulfoxonium Ylides
Perumal Muthuraja, Muhammad Saeed Akhtar, Purushothaman Gopinath, Yong Rok Lee
Abstract
Abstract A substrate‐controlled [4+1] annulation of sulfoxonium ylides with maleimides via Rh(III)‐catalyzed C−H bond activation is developed. The reaction of sulfoxonium ylides with 2‐methyl‐ N ‐arylmaleimides in the presence of AgNTf 2 diastereoselectively provides diversely functionalized indanonylpyrroline‐2,5‐dione derivatives. Furthermore, in the presence of AgBF 4 , the subsequent reaction with maleimides leads to biologically intriguing various spiroindanonylpyrroline‐2,5‐diones. This methodology offers a broad substrate scope, good functional group tolerance, and diastereoselectivity.
Topics & Concepts
ChemistryAnnulationMaleimideCatalysisSubstrate (aquarium)Functional groupScope (computer science)StereochemistryCombinatorial chemistryMedicinal chemistryPolymer chemistryOrganic chemistryProgramming languagePolymerGeologyComputer scienceOceanographyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions