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

Academic Article
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publication date

  • 2005

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.