Rh(III)-Catalyzed C8-Spiroannulation of 1-Aminonaphthalenes with Maleimides
Eunjae Chung, Suho Kim, Amitava Rakshit, Pargat Singh, J.S. Park, Taejoo Jeong, In Su Kim
Abstract
The rhodium(III)-catalyzed C8-spiroannulation of 1-aminonaphthalenes with maleimides is described herein. Initially formed C8-alkenylated 1-aminonaphthalenes can intercept nucleophilic 1-amino groups through the intramolecular aza-Michael reaction, resulting in the formation of spirofused tetracyclic frameworks. This protocol displayed a wide substrate scope and a broad functional group compatibility. The synthetic utility of this process is demonstrated by the gram-scale synthesis, late-stage modification, and synthetic transformations.
Topics & Concepts
Intramolecular forceRhodiumChemistryCatalysisFunctional groupCombinatorial chemistrySubstrate (aquarium)NucleophileMichael reactionStereochemistryOrganic chemistryBiologyEcologyPolymerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthesis and Catalytic Reactions