Alkene Trifluoromethylation-Initiated Remote α‑Azidation of Carbonyl Compounds toward Trifluoromethyl γ‑Lactam and Spirobenzofuranone-Lactam

The
first unprecedented one-pot domino strategy toward diverse
CF3-containing γ-lactam and spirobenzofuranone-lactam
scaffolds of antibacterial armeniaspirole from readily available acyclic
precursors was developed. The key point of this transformation was
the concurrent incorporation of CF3 and azide into the
alkene and remote carbonyl
α-C–H position via carbonyl-stabilized radical intermediate
triggered by alkene trifluoromethylation via a 1,5-H shift in a highly
controlled site-selective manner. Furthermore, gram-scale synthesis
and synthetic applicability of these compounds proved suitable.