An Efficient and General Entry to (Z)-α-Fluoro-β-substituted Acrylaldehydes Based on the Coupling Reaction of α-Fluoro-β-amino Acrylaldehydes with Organolithium Reagents

Abstract

Abstract α-Fluoro-β-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 tetrabutylammonium fluoride (TBAF), reacted smoothly with various organolithium reagents at −78 °C for 0.5 h, followed by hydrolysis with 10% hydrochloric acid at room temperature for 1 h to afford the corresponding (Z)-α-fluoro-β-substituted acrylaldehydes (3) via allylic rearrangement in good to excellent yields.