Direct amino acid-catalyzed asymmetric desymmetrization of meso-compounds: tandem aminoxylation/O-N bond heterolysis reactions.
[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.
Ramachary
Dhevalapally B
DB
The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Barbas
Carlos F
CF
D000588:Amines / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009603:Nitroso Compounds / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D000596:Amino Acids; D007659:Ketones; D009603:Nitroso Compounds; C012456:nitrosobenzene