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Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed C‑Glycosylation

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journal contribution
posted on 06.09.2013, 00:00 by Yaguang Bai, Le Mai Hoang Kim, Hongze Liao, Xue-Wei Liu
An efficient Heck-type C-glycosylation of glycals via the C–N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure α-C-glycosides were obtained when (3R)-glycals were employed, whereas α,β mixtures were observed with (3S)-glycals.