Alkene Trifluoromethylation-Initiated Remote alpha-Azidation of Carbonyl Compounds toward Trifluoromethyl gamma-Lactam and Spirobenzofuranone-Lactam

摘要

The first unprecedented one-pot domino strategy toward diverse CF3-containing gamma-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 alpha-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.