A highly enantioselective oxidative dearomatization of ortho- and para-hydroquinone derivatives to the corresponding masked ortho- and para-benzoquinones has been achieved by using chiral organoiodine(III) catalysts. Importantly, the remote steric effects of the hydrogen-bonding designer organoiodine catalysts allowed us to achieve high chemo- and enantioselectivity for the oxidative dearomatization