Oxidative Remote Aryl Rearrangement of <i>N</i>-Cinnamyl-<i>N</i>-alkoxybenzyl Sulfonamides Using Hypervalent Iodine(III)

An oxidative remote aryl rearrangement of <i>N</i>-cinnamyl-<i>N</i>-alkoxybenzyl sulfonamides with a hypervalent iodine(III) compound was developed to furnish 5,6-disubstituted 1,3-oxazinanes in high yields. This reaction proceeded through the dearomatization of the alkoxybenzene ring on the benzyl group, which acts as a good aryl donor, inducing the regioselective installation of the aryl group and the oxygen atom via cascade transformation. An enantioselective oxidative remote aryl rearrangement using C2-symmetrical chiral iodoarene gave enantioenriched products with high enantioselectivity.