The oxidation of sugar enamines with KMnO4–NaIO4 has been studied. The products depend on the extent of substitution of the enaminic double bond. For 2′-monosubstituted enamines, N-formyl or N-acyl amino sugars are obtained, whereas the 2,2′-disubstituted substrates afforded α-hydroxy amides, together with those products of double-bond cleavage. Z–E Isomerism in the N-formyl amino sugars has been observed.
R. Babiano, C. Durán, J. Plumet, E. Román, E. Sánchez, J. A. Serrano and J. Fuentes, J. Chem. Soc., Perkin Trans. 1, 1989, 1923 DOI: 10.1039/P19890001923
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