3,3′-Diiodobinaphthol and 3,3′-Diiodobiphenol Derivatives as Hypervalent Iodine Organocatalysts for the α-Oxytosylation of Ketones

Abstract

New series of enantiopure 3,3′-diiodobinaphthol- and 3,3′-diiodobiphenol-based molecules have been synthesized and used as chiral hypervalent iodine oxidation organocatalysts in the α-oxytosylation of propiophenone. When we compared these new organocatalysts to our previous series of 3,3′-diiodo-1,1′-binaphthalene-2,2′-diol-fused maleimides, we have made two important observations: the maleimide moiety is the best moiety for obtaining moderate enantioselectivities, and the presence of an aliphatic substituent on the biaryl part of the catalyst enhances the enantioselectivity.

Key words

hypervalence - iodine - organocatalysis - imides - oxidation - stereoselective synthesis

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