An organocatalytic strategy for the stereoselective synthesis of C-galactosides with fluorine at the pseudoanomeric carbon.

The α-fluorination of α- and β-C-ethanals of galactose using Jørgensen catalysts and NFSI was investigated. The crude reaction products were transformed to their primary alcohol or methylenated derivatives, which are versatile precursors to biologically interesting fluorinated glycomimetics. The α-C-glycoside substrate gave moderate to high yields of fluorinated α-C-glycosides with minor amounts of β-C-glycoside analogues.