Synthesis of α-alkylated (Z)-γ-fluoro-β,γ-enoates through organocopper mediated reaction of γ,γ-difluoro-α,β-enoates:: A different reactivity of R3Al-Cu(I) and Me2CuLi

Reaction of gamma,gamma-difluoro-alpha,beta-enoates having a delta-hydroxyl group with trialkylaluminum (R3Al) in the presence of CuI.2LiCl proceeded in S(N)2'-type manner to give a-alkylated (Z)-gamma-fluoro-beta,gamma-enoates, while reductive defluorination of gamma,gamma-difluoro-alpha,beta-enoates with Me2CuLi followed by reaction with alkyl halides provided the corresponding (Z)-alpha-alkylated products.