AN EFFICIENT AND GENERAL ENTRY TO (Z)-ALPHA-FLUORO-BETA-SUBSTITUTED ACRYLALDEHYDES BASED ON THE COUPLING REACTION OF ALPHA-FLUORO-BETA-AMINO ACRYLALDEHYDES WITH ORGANOLITHIUM REAGENTS

alpha-Fluoro-beta-amino acrylaldehydes (2), readily available from the reaction of polyfluoroalkenyl tosylates (1) with dialkylamines in the presence of triethylamine and a catalytic amount (10 mol%) of tetrabu tylammonium fluoride (TBAF), reacted smoothly with various organolithi um reagents at -78 degrees C for 0.5 h, followed by hydrolysis with 10 % hydrochloric acid at room temperture for 1 h to afford the correspon ding (Z)-alpha-fluoro-beta-substituted acrylaldehydes (3) via allylic rearrangement in good to excellent yields.