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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Bibliographic Details
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
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03696