Absolute Configuration of 3,3′-Diphenyl-[2,2′-binaphthalene]-1,1′-diol Revisited
journal contributionposted on 07.08.2009, 00:00 by Prasad L. Polavarapu, Ana G. Petrovic, Sarah E. Vick, William D. Wulff, Hong Ren, Zhensheng Ding, Richard J. Staples
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.