Direct Amino Acid-Catalyzed Asymmetric Desymmetrization of <i>meso</i>-Compounds:  Tandem Aminoxylation/O−N Bond Heterolysis Reactions

Abstract

[reaction: see text] A practical organocatalytic process for the synthesis of optically active, highly substituted alpha-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.