A. M. Genaev, G. E. Salnikov, A. V. Shernyukov, Zh. Zhu, K. Yu. Koltunov, “Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions”, Mendeleev Commun., 2018, Volume 28, Issue 1,Pages <nobr>27–28</nobr>

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Mendeleev Commun., 2018 Volume 28, Issue 1, Pages 27–28 (Mi mendc1651)

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Communications

Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions

A. M. Genaev^a, G. E. Salnikov^ab, A. V. Shernyukov^a, Zh. Zhu^b, K. Yu. Koltunov^bc

^a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
^b Department of Natural Sciences, Novosibirsk State University, Novosibirsk, Russian Federation
^c G.K. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation

Abstract: Compared with the parent 1,1’-bi-2-naphthol (BINOL), its dimethyl ether is highly resistant towards racemization under moderate acidic conditions. This finding confirms the hypothetical mechanism of BINOL atropisomerization including internal rotation around the C¹_sp3 –C^1'_sp3 bond in its protonatedforms.

Language: English

DOI: 10.1016/j.mencom.2018.01.007

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