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

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

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...

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Veröffentlicht in:Journal of organic chemistry 2013-09, Vol.78 (17), p.8821-8825
Hauptverfasser: Bai, Yaguang, Kim, Le Mai Hoang, Liao, Hongze, Liu, Xue-Wei
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Glycosides - chemistry
Glycosylation
Hydrazines - chemistry
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo401032r