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2,2-Difluoro enol silyl ethers were readily prepared by Mg 0 promoted selective defluorination of trifluoromethyl ketones in the presence of TMSCl, which involves C-F bond cleavage.

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[figure: see text] Under hydrogen pressure, a catalytic amount of palladium(II) trifluoroacetate and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) promoted asymmetric hydrogenation of alpha-fluorinated iminoesters to afford highly enantioenriched beta-fluorinated alpha-amino esters. The yield and ee were much improved by employing fluorinated alcohols such as 2,2,2-trifluoroethanol (up to 91% ee).