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

Journal Organic Letters
ISSN: 1523-7060 , E-ISSN: 1523-7052
Output data Year: 2017, Volume: 19, Number: 3, Pages: 532-535 Pages count : 4 DOI: 10.1021/acs.orglett.6b03696
Tags BINOL; MECHANISM; DFT
Authors Genaev Alexander M. 1 , Salnikov George E. 1,2 , Shernyukov Andrey V. 1 , Zhu Zhongwei 2 , Koltunov Konstantin Yu. 2,3
Affiliations
1 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Pr. Akademika Lavrentieva 9, Novosibirsk 630090, Russia
2 Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia
3 Boreskov Institute of Catalysis, Pr. Akademika Lavrentieva 5, Novosibirsk 630090, Russia

Funding (1)

1 Russian Foundation for Basic Research 16-03-00357

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.
Cite: Genaev A.M. , Salnikov G.E. , Shernyukov A.V. , Zhu Z. , Koltunov K.Y.
Protonation Behavior of 1,1′-Bi-2-naphthol and Insights into Its Acid-Catalyzed Atropisomerization
Organic Letters. 2017. V.19. N3. P.532-535. DOI: 10.1021/acs.orglett.6b03696 WOS Scopus РИНЦ ANCAN PMID OpenAlex
Dates:
Submitted: Dec 12, 2016
Published online: Jan 17, 2017
Published print: Feb 3, 2017
Identifiers:
Web of science: WOS:000393539900027
Scopus: 2-s2.0-85011340684
Elibrary: 29479011
Chemical Abstracts: 2017:89109
Chemical Abstracts (print): 166:165533
PMID: 28094529
OpenAlex: W2572709642
Citing:
DB Citing
Web of science 20
Scopus 19
Elibrary 18
OpenAlex 20
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