Palladium(II)-catalyzed transfer vinylation of protected monosaccharides.
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).
Handerson
Sean
S
Guelph-Waterloo Centre for Graduate Work in Chemistry (GWC)(2), Department of Chemistry and Biochemistry, University of Guelph, Guelph, ON, Canada N1G 2W1.
Schlaf
Marcel
M