Synthesis of Diverse Pentasubstituted Pyrroles by a Gold(I)-Catalyzed Cascade Rearrangement-Cyclization of Tertiary Enamide

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.

Automated summary

This article introduces an efficient Au(I)-catalyzed intramolecular cascade reaction, which utilizes propargyl Claisen rearrangement and 5-exo-dig cyclization to prepare a variety of pentasubstituted pyrrole derivatives with excellent yields and functional group tolerance. Scale-up experiments and chemical transformations of the products demonstrate the versatility of tertiary enamides in organic synthesis.