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A combination of nBu4NI and NaIO4 promoted the intermolecular stereo and regioselective bisfunctionalization of glycals in a metal‐free, one‐pot process. The oxidative iodocaboxylation, iodoamination, and iodoazidation of enol ether moieties by employing carboxylic or aromatic acids, and N‐nucleophiles such as 1‐H‐benzotriazole or NaN3 led to glycosyl carboxylates, glycosyl amines, and glycosyl azides, respectively. The protocol is operationally simple, employs readily available and environmental benign reagents, and was applicable for a diverse range of substrates to obtain stereodivergent glycoconjugates in yields up to 99 % with diastereomeric ratios up to 100 %.
Asian Journal of Organic Chemistry – Wiley
Published: Feb 1, 2016
Keywords: ; ; ; ;
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