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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 exemplified with a wide range of glycal donors and acceptors, including substrates bearing alkene functionalities.
- asymmetric catalysis