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 language | English |
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Pages (from-to) | 532-535 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 19 |
Issue number | 3 |
DOIs | |
Publication status | Published - 3 Feb 2017 |
Keywords
- BINOL
- MECHANISM
- DFT