Silyl Lewis Acid-Catalyzed 5- <i>endo-trig</i> Remote Aryl Rearrangement Enabling Dual Migration of Anisole and Amide Groups of <i>N</i> -Cinnamyl- <i>N</i> -alkoxybenzyl Sulfonamides

A silyl Lewis acid-catalyzed 5-<i>endo-trig</i> remote aryl rearrangement of <i>N</i>-cinnamyl-<i>N</i>-alkoxybenzyl sulfonamides in the presence of an oxidant has been developed, affording 5-substituted oxazolidines in high yields. This reaction proceeds through the dearomatization of the arene moiety on the alkoxybenzyl group. Furthermore, derivatization of the oxazolidine product via terminal carbon-selective ring opening of the corresponding aziridine intermediate with various nucleophiles triggers a dual migration of the anisole and amide moieties, highlighting the broad synthetic potential of this remote aryl rearrangement.