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

A silyl Lewis acid-catalyzed 5-endo-trig remote aryl rearrangement of N-cinnamyl-N-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.