Synthesis of Diverse Pentasubstituted Pyrroles by a Gold(I)-Catalyzed Cascade Rearrangement-Cyclization of Tertiary Enamide
Wenzhong Li, Ran Shi, Sen Chen, Xuesi Zhang, Peng Wei, Si Chen, Jiazhu Li, Xin‐Ming Xu, Yanping Zhu, Xueyuan Wang
Abstract
An efficient Au(I)-catalyzed intramolecular cascade reaction of tertiary enamides tethered an alkynyl group has been developed. The process is composed of a propargyl-claisen rearrangement and 5-exo-dig cyclization. This protocol provided a powerful method for the preparation of a variety of pentasubstituted pyrroles derivatives with excellent functional group tolerance in excellent yields. Scale-up experiment and chemical transformations of products exhibited the versatility of tertiary enamides in organic synthesis again.
Topics & Concepts
ChemistryPropargylFunctional groupCascadeCatalysisIntramolecular forceCascade reactionCombinatorial chemistryClaisen rearrangementOrganic chemistryStereochemistryChromatographyPolymerCatalytic Alkyne ReactionsSynthesis and Characterization of PyrrolesCatalytic C–H Functionalization Methods