New routes to highly functionalised heterocyclic compounds from cyclopropanes

Heterocyclic compounds are of great importance in the pharmaceutical industry as well as academic research so key methodology, which generates a highly functionalized medium ring in the minimum number of steps, is of great interest. This project addresses this challenge by looking at the formation of pyrrolidines and furans from cyclopropanes via a [2+3] cycloaddition reaction in a highly atom efficient approach. Prior to our work in this field, Tsuji and others have shown the formation of a zwitterionic π-allyl palladium complex derived from vinylcyclopropanes and naphthalenes is possible. During the project, we have improved the understanding of the formation of zwitterionic π-allyl palladium complexes in aromatic systems. [Continues.]