It is well established that the Van der Waals radii of fluorine (rF-q.35 A) and hydrogen (rH-1.10 /~) are quite similar, thereby rendering fluorine the only element that can replace hydrogen in biological systems without changing steric demands. 1 However, the strong electronegative nature of fluorine, relative to that of hydrogen, imparts a strong electron-withdrawing inductive effect causing substantial differences in the reactivity of neighboring functional groups. Consequently, site-specific fluorination of organic molecules has attracted interest for applications in polymer, medicinal, and agricultural chemistry.2 Fluorinated acrylic esters, in particular, are interesting sythons due to their prolific chemistry and potential for further elaboration into fluorinated analogs of natural products. For example, fluoroacrylic esters are excellent Michael acceptors and have been employed as such in the synthesis of ,/-fluoroglutamic acid derivatives, 3 angiotensin II derivatives, 3 and a fluorinated analog of Captopril, an angiotensin converting enzyme inhibitor. 4 a-Trifluoromethylacrylic acid has found utility in the preparation of trifluoromethyluracil derivatives v/a an annulation process. 5 Furthermore, fluoroacrylic esters are suitable dienophiles for Diels-Alder cycloadditions, and have been employed as dienophiles in the synthesis 6-trifluoromethylshikimic acid 6 and a fluorinated analog of retinal. 7 Fluoroacrylic esters of the type CFH=CHCO2R,8 CH2=CFCO2R, 9 CF2=CHCO2R,10 CH2=C(CFa)CO2R, it (E)-CF3CH=CHCO2R, 12 and (Z)-CF3CH=CHCO2R 6 have been prepared by multistep sequences in which the ct,13-unsaturated double bonds were introduced late in the synthesis by [3-elimination reactions. Other approaches to fluorinated acrylates involved the quenching of fluorovinyllithium reagents with CO2 at low temperatures,~0b.Hb. 13 condensation reactions with hexafluoroacetone for the synthesis of (CF3)2C=CHCO2R, 14 Ojima's synthesis of CH2=C(CF3)CO2H v/a palladium-catalyzed carbonylation of CH2=C(CF3)Br, 5 and palladium-catalyzed cross-coupling of (Z)-RCF=CFZnCI with ethyl chloroformate. 15 However, in our hands, (Z)-PhCF=CFZnI coupled with CICO2Et under palladium catalysis to give only low yields of the corresponding ester.16 The lack of general and convenient methodology for the stereospecific synthesis of (E)-and (Z)-ct, ~-difluoroacrylate ester derivatives and ct, [3-difluorocinnamate esters has impeded the investigation of this interesting class of compounds.