Enantioselective Synthesis of Masked Benzoquinones Using Designer Chiral Hypervalent Organoiodine(III) Catalysis

Abstract

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 of para-hydroquinone derivatives through an associative iodine(III)–phenoxide intermediate.