Stereoselective Chiral Recognition of Amino Alcohols with 2,2′‑Dihydroxybenzil

2,2′-Dihydroxybenzil
is demonstrated to be a highly diastereoselective
stereodynamic receptor for the chiral recognition of amino alcohols.
The receptor by forming diimine compounds with amino alcohols showed
good (11:1) to excellent (>50:1) diastereoselectivity in chloroform.
The existence of intramolecular hydrogen bonding with amino alcohols
only in an axial conformer is demonstrated by 1H NMR and
CD spectroscopy, X-ray crystallography, and DFT computations. The
exciton chirality method can be used with diazo-attached 2,2′-dihydroxybenzil.