Organic Letters
Organic Letters
5 years ago

Reversal of Enantioselectivity Approach to BINOLs via Single and Dual 2-Naphthol Activation Modes

Reversal of Enantioselectivity Approach to BINOLs via Single and Dual 2-Naphthol Activation Modes
Kyungsoo Oh, Hun Young Kim, Shinobu Takizawa, Hiroaki Sasai
A mechanism-driven enantiodivergent approach to chiral 1,1′-bi-2-naphthols via catalytic asymmetric oxidative coupling of 2-naphthol derivatives is described for the first time. By utilizing 2-naphthol derivatives with low oxidation potential, the substrates were activated by either chiral mononuclear or dinuclear vanadium(V) catalyst to promote distinctively different asymmetric reaction pathways: single versus dual substrate activation mechanisms.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01734

DOI: 10.1021/acs.orglett.7b01734

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