Intramolecular radical rearrangement reactions of 2-methyleneaziridines: Application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines
N. Prevost et M. Shipman, Intramolecular radical rearrangement reactions of 2-methyleneaziridines: Application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines, ORG LETT, 3(15), 2001, pp. 2383-2385
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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.