Gold-catalyzed formal (3+2) and (4+2) cycloadditions of alkynes to highly functionalized dihydropyrroles and tetrahydropyridines

Herein, we report a gold-catalyzed formal cycloaddition reaction of readily available alkynes using amino but/pent-2-enoate derivatives as annulating reagents. The new strategy provides a straightforward and convergent route towards the synthesis of highly functionalized 2,3-dihydropyrroles and 1,2,3,4-tetrahydropyridines with high efficiency and a broad substrate scope. Moreover, the reaction could be facilely performed at the millimole scale and the products could be further transformed into other valuable classes of N-heterocycles.

Automated summary

This research reports a new gold-catalyzed formal cycloaddition reaction that utilizes readily available alkynes and amino but/pent-2-enoate derivatives as reactants to synthesize highly functionalized 2,3-dihydropyrroles and 1,2,3,4-tetrahydropyridines. The reaction shows high efficiency and a broad substrate scope, and can be easily performed at the millimole scale. The resulting products can be further transformed into other valuable N-heterocycles.