Gold-catalyzed amination of in situ formed alkyl gold species with p-quinonediimines as a N source

Abstract

Herein, a gold-catalyzed electrophilic propargyl amination reaction of N-propargylamide using p-quinonediimines as a N source has been presented. This reaction initiates via a gold-catalyzed 5-exo-dig cyclization of N-propargylamides to form the key alkylgold species under basic conditions, followed by electrophilic addition with p-quinonediimines, leading to functionalized alkylideneoxazolines with a nitrogen-containing tertiary carbon center in good to high yields under mild reaction conditions. Further synthetic transformations of the obtained products offer a complementary approach for the assembly of poly-substituted oxazole derivatives, which are difficult to access by other methods.