Synthesis of meta -Aminophenol Derivatives via Cu-Catalyzed [1,3]-Rearrangement-Oxa-Michael Addition Cascade Reactions.

Cu-catalyzed reactions of N -alkoxy-2-methylanilines and alcohols in the presence of catalytic amounts of IPrCuBr and AgSbF 6 afforded the corresponding meta -aminophenol derivatives in good to high yields. These reactions proceed via a [1,3]-rearrangement, in which the alkoxy group migrates from the nitrogen atom to the methyl-substituted ortho position, followed by an oxa-Michael reaction of the resulting ortho -quinol imine intermediate.