Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides
Mingshuai Zhang, Longkun Chen, Haifeng Sun, Zhuoyuan Liu, Jiuzhong Huang, Fuchao Yu
Abstract
An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones and iodonium ylides has been developed. The novel strategy allows for access to a new class of structurally diverse tetrahydro-indolones with high efficiency and a broad substrate scope. In addition, this transformation represents the first example of the selective Rh(III)-catalyzed alkenyl C-H bond functionalization and annulation of enaminones. Finally, the potential applications of this protocol are demonstrated through gram-scale reaction and late-stage modification.
Topics & Concepts
AnnulationChemistryCatalysisCombinatorial chemistrySubstrate (aquarium)Surface modificationScope (computer science)StereochemistryMedicinal chemistryOrganic chemistryComputer scienceGeologyProgramming languagePhysical chemistryOceanographyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms