Novel synthesis of (Z)-difluoroacrylates via a highly stereoselective addition-elimination reaction.
On treating readily prepared benzyl 2,3,3-trifluoroacrylate with various Grignard reagents, e.g., aryl-, alkyl-, or alkenylmagnesium halide, in the presence of a catalytic amount of copper(I) salt in THF at -78 degrees C for 1 h, the corresponding alpha,beta-difluoroacrylates were obtained in 54-98% yields with high Z-selectivity.
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
Shigeyuki
S
Yamada
Mayumi
M
Noma
Tsutomu
T
Konno
Takashi
T
Ishihara
Hiroki
H
Yamanaka