Stereoselective syntheses of (Z)-fluoroalkenoates 3a−g have been developed in three steps from the readily available fluorosulfide 5 and aldehydes. This preparation, involving a Durst reaction, was highly stereoselective and led to fluoroalkenes in 50−60% overall yields, without purification of intermediates.It is well-established that the replacement of hydrogen atoms of organic molecules by fluorine atoms strongly modifies their chemical, physical, and biological properties. Several applications reported the enhancement of the half-life of drugs due to the high stability of the carbon-fluorine bond or the synthesis of suicide inhibitors induced by the elimination of fluorine atom during the metabolization process. 1 Toward this goal, the fluorovinylic moiety has been introduced in various bioactive compounds such as sex pheromones, ribonucleotides, or retinal analogues. 2 The widely used strategy to build (E)-fluoroalkenoates from aldehydes is the Horner-Wadsworth-Emmons reaction (HWE), involving the commercially available triethyl 2-fluoro-2-phosphonoacetate. 3 Alternative approaches based on concerted elimination of -mesyloxy sulfoxides afforded (E)-fluoroalkenes with moderate selectivity. 4 Concerning the preparation of the Z isomer, the most elegant and direct approach consisted of alkylating the ethyl phenylsulfinyl fluoroacetate to produce exclusively (Z)-fluoropropenoates by a stereoselective elimination of sulfenic acid. 5 On the other hand, a phenylselenenyl fluoride equivalent has been used to produce (Z)-fluoroalkenoates from diazoesters. 6 Few methods have reported the selective synthesis of (Z)-fluoroalkenoates from aldehydes. The most efficient are the zinc-copper chloride promoted reaction of methyl difluoroacetate with carbonyl compounds, 7 the Peterson olefination involving aldehydes and R-fluoro-R-silyl acetate as a starting building block, 8 and the transformation of fluorinated sym-(1) Welch, J. T. Tetrahedron 1987, 43, 3123-3197. (2) Camps, F.; Coll, J.; Fabrias, G.; Guerrero, A. Tetrahedron 1984, 40, 2871-2878. McCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7339-7440. Francesh, A.; Alvarez, R.; Lopez, S.; de Lera, A. R.