Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines.
[reaction: see text] Intramolecular 5-exo cyclization of 3-(2-methyleneaziridin-1-yl)propyl radicals leads to the generation of a highly strained, bicyclic aziridinylcarbinyl radical that undergoes C-N bond fission to the ring-expanded aminyl radical. This methodology provides access to substituted 3-methylenepiperidines and, by combining it with an additional 5-exo-trig cyclization reaction, the octahydroindolizidine skeleton.
Prévost
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School of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK.
Shipman
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