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Organic letters

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


PMID 15816756

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.

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N24609
Nitrosobenzene, ≥97%
C6H5NO