Copper-Catalyzed Ring Expansion of Vinyl Aziridines

Copper-Catalyzed Ring Expansion of Vinyl Aziridines under Mild Conditions: E. Tosi, K. Spielmann, R. M. de Figueiredo, J.-M. Campagne

Synlett 2020, 31, DOI: 10.1055/s-0040-1706007


Vinyl aziridines are highly versatile building blocks that can be synthesized using a variety of different methods, such as the reaction of nitrenes with conjugated dienes, the reaction of allylic carbenes with imines or rearrangement reactions of pyridinium salts and pyrroles. Within the frame of a research program aimed at identifying novel applications of vinyl aziridines, recently the group of Dr. Renata Marcia de Figueiredo and Professor Jean-Marc Campagne from the University of Montpellier (France) described a synthetically useful ring-expansion reaction promoted by copper(II) triflate.

Professor Campagne said: “Thanks to a serendipitous finding, we developed very mild and practical conditions for the synthesis of 3-substituted pyrrolines from accessible vinyl aziridines. Even though efforts are needed to improve the reaction scope, this might be an efficient method for the synthesis of 3-pyrrolines, which are useful building blocks in both organic and medicinal chemistry.”

Get Trial Access to the chemistry journals
Download SYNFORM or read it online