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Teaching an old molecule new tricks: A new solution for an expeditious C-sialylation from N-acetylneuraminic acid involves the use of the peracetylated derivative 1, a very common starting material prepared 40 years ago in Heidelberg, through an anomeric umpolung by samarium diiodide without an additive, in the presence of a carbonyl compound. Excellent yields are obtained for the coupling with cyclic ketones (see scheme).
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Malapelle et al. (2006) studied this question.
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