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 journalArticlepeer-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 languageEnglish
Pages (from-to)532-535
Number of pages4
JournalOrganic Letters
Volume19
Issue number3
DOIs
Publication statusPublished - 3 Feb 2017

Keywords

  • BINOL
  • MECHANISM
  • DFT

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