Fluorinated Amine Stereotriads via Allene Amination

The incorporation
of fluorine into organic scaffolds often improves
the bioactivity of pharmaceutically relevant compounds. C–F/C–N/C–O
stereotriad motifs are prevalent in antivirals, neuraminidase inhibitors,
and modulators of androgen receptors, but are challenging to install.
An oxidative allene amination strategy using Selectfluor rapidly delivers
triply functionalized triads of the form C–F/C–N/C–O,
exhibiting good scope and diastereoselectivity for all syn products. The resulting stereotriads are readily transformed into
fluorinated pyrrolidines and protected α-, β-, and γ-amino
acids.