Generation and Cycloaddition of Polymer-Supported Azomethine Ylide via a 1,2-Silatropic Shift of α-Silylimines: Traceless Synthesis of Pyrrolidine Derivatives

The 1,3-dipolar cycloaddition of polymer-supported azomethine ylides to dipolarophiles gave pyrrolidine derivatives in good yields. The azomethine ylides were generated from resin-bound alpha-silylimines via a 1,2-silatropic shift. The features of this method are not only a traceless synthesis but also a unique solid-phase route to pyrrolidines with extensive diversity. [reaction: see text]