Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative Spirolactonization of Naphthol Derivatives.

Highly enantioselective oxidative dearomatization of 2-naphthol derivatives was achieved for the first time by using conformationally flexible organoiodine catalysts derived from 2-aminoalcohol as a chiral source. Moreover, with the use of these catalysts, excellent enantioselectivities were also achieved for 1-naphthol derivatives, which had previously been obtained with only lower enantioselectivities. Furthermore, the product obtained from the present reaction could be transformed to a highly functionalized spirolactone in high yield and with excellent stereoselectivity.