Reactive dienes: Intramolecular aromatic oxidation of 3-(2-hydroxyphenyl)-propionic acids

Treatment of 3-(2-hydroxyphenyl)-propionic acids with a hypervalent iodine reagent in the presence of a dienophile initiates a tandem intramolecular aromatic oxidation/Diels-Alder reaction. Herein we report (1) investigations on the scope and limitations of this novel reaction combination and (2) preliminary diastereoselectivity studies using alpha- and beta-substituted acids.