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Synlett 1998; 1998(7): 721-722
DOI: 10.1055/s-1998-1765
DOI: 10.1055/s-1998-1765
letter
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Mild, Racemization Free Cleavage of Ketone SAMP-Hydrazones with Oxalic Acid - Recycling of the Chiral Auxiliary
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
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Cleavage of ketone SAMP-hydrazones 1a-f with a saturated aqueous oxalic acid solution gives the corresponding ketones 2a-f in excellent yields and with high enantiomeric purity (ee = 90-99%). The chiral auxiliary SAMP is recovered from the aqueous phase in good yield (85%) and with unchanged enantiomeric purity. This racemisation free cleavage procedure is compatible with functionalities sensitive to oxidative cleavage conditions, such as ozonolysis, or to strong acids.
hydrazone cleavage - SAMP hydrazones - oxalic acid - auxiliary recycling - optically active ketones