Aliphatic amides are selectively functionalized at the gamma- and delta-positions through directed radical 1,5 and 1,6 H-abstractions, respectively, The initially gamma- or delta-lactams are intercepted. by N-iodosuccinimide and trimethylsilyl azide, leading to double and triple C-H functionalizations at the gamma, delta-, and epsilon-positions. This new reactivity is exploited to convert alkyls into amino alcohols and allylic amines.