Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: Tandem aminoxylation/O-N bond heterolysis reactions

Abstract

(Chemical Equation Presented) A practical organocatalytic process for the synthesis of optically active, highly substituted α-hydroxy-ketones was achieved through asymmetric desymmetrization (ADS) of prochiral ketones. The ADS and O-N bond reduction reaction of prochiral ketone with nitrosobenzene in the presence of a catalytic amount of chiral amine or amino acid produced the tandem ADS/O-N bond reduced products as single diastereomers with good yields and excellent enantiomeric excesses. © 2005 American Chemical Society.