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
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<I>α</I>-Fluoro-<I>β</I>-amino acrylaldehydes (<B>2</B>), readily available from the reaction of polyfluoroalkenyl tosylates (<B>1</B>) 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 (<I>Z</I>)-<I>α</I>-fluoro-<I>β</I>-substituted acrylaldehydes (<B>3</B>) <I>via</I> allylic rearrangement in good to excellent yields.
- Chemistry Letters
Chemistry Letters 1997(8), 739-740, 1997-08
The Chemical Society of Japan