Short synthetic preparation of enantiomerically pure tetrafluoroethylenated sugar derivatives

Novel and short synthetic approaches to 2,3-dideoxy-2,2,3,3-tetrafluoropyranoses or azapyranoses have been developed successfully using commercially available reagents, such as 4-bromo-3,3,4,4-tetrafluoro-1-butene. This synthetic strategy involves an intermolecular reductive coupling of 4-bromo-3,3,4,4-tetrafluoro-1-butene and various chiral aldehydes using LiBr-free MeLi as a key transformation.