Asymmetric oxidation of 1,2-diols using N-bromosuccinimide in the presence of chiral copper catalyst

Asymmetric oxidation of 1,2-diols using N-bromosuccinimide (NBS) in the presence of copper(II) triflate and (R,R)-Ph-BOX has been exploited. This oxidation was applicable to asymmetric desymmetrization of meso-hydrobenzoin and kinetic resolution of dl-hydrobenzoin and racemic-cycloalkane-cis-1,2-diols to afford optically active alpha-ketoalcohols with good to high enantiomeric excess. (C) 2007 Elsevier Ltd. All rights reserved.