Chemistry Letters, Vol.31, No.1, 28-29, 2002
Synthesis of alpha-alkylated (Z)-gamma-fluoro-beta,gamma-enoates through organocopper mediated reaction of gamma,gamma-difluoro-alpha,beta-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.