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Updated: Jun 22, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited
Prasad L Polavarapu1, Ana G Petrovic, Sarah E Vick
1Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, USA. Prasad.L.Polavarapu@vanderbilt.edu
Abstract:
The experimental vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion spectra and corresponding quantum chemical predictions of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol (VANOL) are used to confirm its absolute configuration as (+)(589)-(aR) or (-)(589)-(aS). A discrepancy in the literature crystal structure has been resolved by determining the X-ray crystal structure of the brucine binaphtholphosphate salt of the (aS)-enantiomer of VANOL.
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