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Genaev, Alexander M; Salnikov, George E; Shernyukov, Andrey V; Zhu, Zhongwei; Koltunov, Konstantin Yu
Organic letters, 02/2017, Letnik: 19, Številka: 3Journal Article
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.
