Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Chiral Atropisomeric 8,8′-Diiodobinaphthalene for Asymmetric Dearomatizing Spirolactonizations in Hypervalent Iodine Oxidations

Chiral Atropisomeric 8,8′-Diiodobinaphthalene for Asymmetric Dearomatizing Spirolactonizations in Hypervalent Iodine Oxidations
Naoko Takenaga, Mihoyo Fujitake, Toshifumi Dohi, Keitaro Miyazaki, Yasuyuki Kita, Hirotaka Sasa
A new type of binaphthyl-based chiral iodide functionalized at positions 8 and 8′ of the naphthalene rings has been found as a promising structural motif for the asymmetric hypervalent iodine(III) oxidations, specifically, for the dearomatizing spirocyclization of naphthol carboxylic acids showing expectedly better enantioselectivities versus other atropisomeric biaryls, i.e., a conventionally used binaphthalene having the diiodides in the minor groove.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02037

DOI: 10.1021/acs.joc.7b02037

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