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

Alexander M. Genaev; George E. Salnikov; Andrey V. Shernyukov; Zhongwei Zhu; Konstantin Yu Koltunov

doi:10.1021/acs.orglett.6b03696

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

Alexander M. Genaev, George E. Salnikov, Andrey V. Shernyukov, Zhongwei Zhu, Konstantin Yu Koltunov

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	532-535
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.6b03696
Publication status	Published - 3 Feb 2017

Keywords

BINOL
MECHANISM
DFT

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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",

abstract = "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.",

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AU - Salnikov, George E.

AU - Shernyukov, Andrey V.

AU - Zhu, Zhongwei

AU - Koltunov, Konstantin Yu

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N2 - 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.

AB - 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.

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