Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization

The behavior of 1,1′-bi-2-naphthol (BINOL) in variety of (super)­acid media has been studied by NMR. The results are combined with the theoretical (DFT) study of the role of mono- and diprotonated forms of BINOL in the acid-catalyzed atropisomerization of this compound. It is demonstrated that the p...

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Published in:Organic letters 2017-02, Vol.19 (3), p.532-535
Main Authors: Genaev, Alexander M, Salnikov, George E, Shernyukov, Andrey V, Zhu, Zhongwei, Koltunov, Konstantin Yu
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container_title Organic letters
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creator Genaev, Alexander M
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description The behavior of 1,1′-bi-2-naphthol (BINOL) in variety of (super)­acid media has been studied by NMR. The results are combined with the theoretical (DFT) study of the role of mono- and diprotonated forms of BINOL in the acid-catalyzed atropisomerization of this compound. It is demonstrated that the process of enantiomeric configuration exchange proceeds mainly via internal rotation around the C1­(sp3)–C1′(sp3) bond in intermediates such as C1-monoprotonated keto or C1,C1′-diprotonated forms of BINOL, depending on the acidity level.
doi_str_mv 10.1021/acs.orglett.6b03696
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title Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization
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