A Facile Synthesis of N-[2-(Trifluoromethyl)allyl]amides and Their Transformation into Angularly Trifluoromethylated Bicyclic Cyclopentenones
On treatment with <I>sec</I>-BuLi at −105 °C, 2-bromo-3,3,3-trifluoropropene undergoes rapid lithium–halogen exchange to generate thermally unstable 1-(trifluoromethyl)vinyllithium, which reacts with <I>N</I>-tosylimines to afford <I>N</I>-[2-(trifluoromethyl)allyl]amides in high yield. Propargylation of the amides, followed by the Pauson–Khand reaction, readily provides pyrrolidine ring-fused cyclopentenones with an angular trifluoromethyl group.
- Chemistry letters
Chemistry letters 36(1), 22-23, 2007-01-05
The Chemical Society of Japan