Palladium-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals.
Palladium(II) in combination with a monodentate phosphine ligand enables the unprecedented direct and α-stereoselective catalytic synthesis of deoxyglycosides from glycals. Initial mechanistic studies suggest that in the presence of N-phenyl-2-(di-tert-butylphosphino)pyrrole as the ligand, the reaction proceeds via an alkoxy palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is demonstrated with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.
['Sau|Abhijit|A|', 'Williams|Ryan|R|', 'Palo-Nieto|Carlos|C|', 'Franconetti|Antonio|A|', 'Medina|Sandra|S|', 'Galan|M Carmen|MC|0000-0001-7307-2871']
deoxyglycosides palladium acetals asymmetric catalysis glycosylation