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

2017; American Chemical Society; Volume: 82; Issue: 22 Linguagem: Inglês

10.1021/acs.joc.7b02037

1520-6904

Toshifumi Dohi, Hirotaka Sasa, Keitaro Miyazaki, Mihoyo Fujitake, Naoko Takenaga, Yasuyuki Kita,

Alkaloids: synthesis and pharmacology

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.