Generation and cycloaddition of polymer-supported azomethine ylide by utilizing the characteristics of silicon: a facile route to pyrrolidines and pyrroles from α-silylimines bound to resin

The solid-phase synthesis of pyrrolidine and pyrrole derivatives using polymer-supported α-silylimines is described. Polymer-supported azomethine ylides were generated from the corresponding α-silylimine by thermal 1,2-silatropy onto the imino nitrogen or by treatment with a trifluorosilane as a quaternization and desilylation reagent, and the resulting species were then reacted with dipolarophiles to give five-membered heterocycles.