Unprotected aldose sugars are smoothyl decarbonylated by 1 equiv. of chlorotris(triphenylphosphine)rhodium in N-methylpyrrolidin-2-one at 130 °C to give the next lower alditol and carbonylchlorobis(triphenylphosphine)rhodium; ketose sugars undergo more complex dehydration–decarbonylation reactions.
M. A. Andrews and S. A. Klaeren, J. Chem. Soc., Chem. Commun., 1988, 1266 DOI: 10.1039/C39880001266
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