Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited

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.