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

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

Authors

Genaev Alexander M. ¹ , Salnikov George E. ^1,2 , Shernyukov Andrey V. ¹ , Zhu Zhongwei ² , Koltunov Konstantin Yu. ^2,3

Affiliations

1	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Pr Akad Lavrentieva 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Boreskov Inst Catalysis, Pr Akad Lavrentieva 5, Novosibirsk 630090, Russia

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 Cl(sp(3))-Cl'(sp(3)) bond in intermediates such as Cl-monoprotonated keto or Cl,Cl'-diprotonated forms of BINOL, depending on the acidity level.

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

Published online:	Jan 17, 2017
Published print:	Feb 3, 2017

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