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.
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