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Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization. / Genaev, Alexander M.; Salnikov, George E.; Shernyukov, Andrey V. et al.

In: Organic Letters, Vol. 19, No. 3, 03.02.2017, p. 532-535.

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

Harvard

Genaev, AM, Salnikov, GE, Shernyukov, AV, Zhu, Z & Koltunov, KY 2017, 'Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization', Organic Letters, vol. 19, no. 3, pp. 532-535. https://doi.org/10.1021/acs.orglett.6b03696

APA

Genaev, A. M., Salnikov, G. E., Shernyukov, A. V., Zhu, Z., & Koltunov, K. Y. (2017). Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization. Organic Letters, 19(3), 532-535. https://doi.org/10.1021/acs.orglett.6b03696

Vancouver

Genaev AM, Salnikov GE, Shernyukov AV, Zhu Z, Koltunov KY. Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization. Organic Letters. 2017 Feb 3;19(3):532-535. doi: 10.1021/acs.orglett.6b03696

Author

Genaev, Alexander M. ; Salnikov, George E. ; Shernyukov, Andrey V. et al. / Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization. In: Organic Letters. 2017 ; Vol. 19, No. 3. pp. 532-535.

BibTeX

@article{16a3b927c8fb415e83eae6216280e44d,
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.",
keywords = "BINOL, MECHANISM, DFT",
author = "Genaev, {Alexander M.} and Salnikov, {George E.} and Shernyukov, {Andrey V.} and Zhongwei Zhu and Koltunov, {Konstantin Yu}",
year = "2017",
month = feb,
day = "3",
doi = "10.1021/acs.orglett.6b03696",
language = "English",
volume = "19",
pages = "532--535",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "3",

}

RIS

TY - JOUR

T1 - Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization

AU - Genaev, Alexander M.

AU - Salnikov, George E.

AU - Shernyukov, Andrey V.

AU - Zhu, Zhongwei

AU - Koltunov, Konstantin Yu

PY - 2017/2/3

Y1 - 2017/2/3

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.

KW - BINOL

KW - MECHANISM

KW - DFT

UR - http://www.scopus.com/inward/record.url?scp=85011340684&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b03696

DO - 10.1021/acs.orglett.6b03696

M3 - Article

C2 - 28094529

AN - SCOPUS:85011340684

VL - 19

SP - 532

EP - 535

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 3

ER -

ID: 9048276