Hypervalent organoiodine reagents in the transannular functionalisation of medium-sized lactams: synthesis of 1-azabicyclo compounds

Abstract

The amidyl radical intermediates, produced by photolysis of medium-sized lactams 7-heptanelactam (1), 8-octanelactam (3), and 9-nonanelactam (6) in the presence of (diacetoxyiodo)benzene (DIB) and iodine, undergo transannular hydrogen abstraction to afford intermolecularly functionalised compounds such as oxoindolizidines (4) and (5) and the 1-azabicyclo[5.3.0]decan-2-one (7) that are obtained in high yield from lactams (3) and (6), respectively.