A new organocatalytic asymmetric Michael addition reaction by cleavage of carbon-carbon bonds through a mild release of trifluoroacetate has been developed. The reported method generates the decarboxylated γ-nitro-α-fluorocarbonyl products with excellent enantioselectivies (up to 98% ee) and good diastereoselectivies (up to 20:1 dr).

The gem-difluoromethylenated acetonide 2 was efficiently synthesized as new precursor of HMG-CoA reductase inhibitor. Straightforward olefination via Pd-catalyzed C⁴-H activation of 1,3,5-trisubstituted pyrazoles 1 was proceeded smoothly in the presence of Pd(OAc)₂ and AgCO₃. This protocol has merits in terms of the improved atomic economy and prevention from the generation of by-products.

In the presence of In/CuCl, ethyl 4-bromo-4,4-difluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate reacted with various aldehydes in aqueous medium at room temperature to give the α,α-difluorinated β-hydroxy carbonyl compounds. Furthermore, treating Reformatsky addition compounds with 1 equiv. of sodium hydroxide in the mixture of tetrahydrofuran and water afforded gem-di?uoromethylenated 2-triphenylphosphoranylidene δ-lactones in excellent yields.

A sequential transformation of fluoroalkylated adducts obtained from ethyl 3-hydroxy-4-pentenoate with fluorinated iodides was reported. The dehydrohalogenation of adducts was favored to give fluoroalkylated unsaturated β-hydroxy esters in the presence of triethylamine. And intramolecular S_N2 reaction products, fluoroalkylated β,γ-epoxy esters, were obtained in 10% aqueous sodium carbonate solution.