Synthesis of Azepane Derivatives via Formal 1,3-Migration of Hydroxy and Acyloxy Groups and Selective Annulation
Zijuan Feng, Hongjian Jiao, Zihang Ye, Ye Jie, Ze‐Feng Xu, Shengguo Duan, Chuan‐Ying Li
Abstract
Formal 1,3-migration of hydroxy and acyloxy groups initiated by α-imino rhodium carbene was achieved, and the following selective annulations of the corresponding zwitterions could efficiently afford azepane derivatives. Benefiting from a time-saving procedure as well as a good functional group tolerance, this unique migration–annulation protocol could provide an efficient tool for synthesizing seven-membered N-heterocycles. The plausible mechanism is discussed.
Topics & Concepts
AnnulationChemistryRhodiumFormal synthesisCombinatorial chemistryCarbeneFunctional groupStereochemistryTotal synthesisOrganic chemistryCatalysisPolymerCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry Methods