Palladium(II)-catalyzed transfer vinylation of protected monosaccharides.
ORGANIC LETTERS(2002)
Abstract
A method for the catalytic vinylation of protected monosaccharides bearing a single free hydroxyl function has been developed. Reaction of representative primary, secondary, and anomeric sugar hydroxyl functions with butyl vinyl ether as the reactant and solvent and (phen)Pd-(OAc)(2) (phen = 1,10-phenanthroline ligand) as the catalyst gives the corresponding vinylated sugar products in 36-79% yield. The catalyst requires the presence of traces of oxygen in the reaction mixture to prevent decomposition to Pd(0).
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Key words
protected monosaccharides,transfer vinylation,palladiumii-catalyzed
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