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

Org Lett. 2005 Apr 14;7(8):1577-80. doi: 10.1021/ol050246e.


[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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amines / chemistry
  • Amino Acids / chemistry*
  • Combinatorial Chemistry Techniques*
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Molecular Structure
  • Nitroso Compounds / chemistry
  • Stereoisomerism


  • Amines
  • Amino Acids
  • Ketones
  • Nitroso Compounds
  • nitrosobenzene