title: Intramolecular radical rearrangement reactions of 2-methyleneaziridines: application to the synthesis of substituted piperidines, decahydroquinolines, and octahydroindolizines.
abstract: [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.
authors.affiliation: School of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK.
authors.forename: N
authors.initials: N
authors.lastname: Prévost
authors.forename: M
authors.initials: M
authors.lastname: Shipman