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First example of the carbon-Ferrier rearrangement of glycals with isocyanides: a novel synthesis of C-glycosyl amides

✍ Scribed by J.S. Yadav; B.V. Subba Reddy; D. Narasimha Chary; C. Madavi; A.C. Kunwar

Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 239 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.10.090

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✦ Synopsis

Glycals undergo smooth carbon-Ferrier rearrangement with isocyanides in the presence of a catalytic amount of FeCl 3 under mild reaction conditions to provide C-glycosyl amides in good yields with high a-selectivity. The use of FeCl 3 makes this method simple, convenient and cost-effective. This is the first report on carbon-Ferrier rearrangement using isonitriles as nucleophiles.

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