Intramolecular radical rearrangement reactions of 2-methyleneaziridines: Application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines

[GRAPHICS] Intramolecular 5-exo cyclization of 3-(2-methyleneaziridin-1-yl)propyl radi cals leads to the generation of a highly strained, bicyclic aziridinylcarbi nyl radical that undergoes C-N bond fission to the ring-expanded aminyl rad ical. This methodology provides access to substituted 3-methylenepiperidine s and, by combining it with an additional 5-exo-trig cyclization reaction, the octahydroindolizidine skeleton.