The 1,2,2'-trisubstituted olefins are challenging substrates for intramolecular asymmetric aziridination. A cyclic 1,2,2'-trisubstituted olefin 1t gave 2t in 83% yield and an improved 42% ee over our previous result with a carbamate substrate. A cyclic 1,2,2'-trisubstituted olefin derived from (1R)-(-)-nopol gave a single diastereomer of the corresponding aziridine 2u in near-quantitative yield (see the SI for assignments of relative stereochemistry using NOESY). In addition to the [4.1.0] bicyclic aziridine products, other azabicyclic patterns were also explored. A disubstituted allylic carbamimidate 1v affords a five-membered ring product 2v in good 79% ee after isolation, presumably due to ring-opening of the corresponding aziridine (see Figure footnote for details). Moderate yields and ee of other five-membered ring products were obtained from trisubstituted allylic carbamimidates 1w and 1x. Alkene migration was also observed as a result of fast ring-opening of the [3.1.0] bicyclic aziridines. Sevenmembered ring formation (2y) was not detected (only the allylic C-H insertion product 2y' was obtained). Aziridination was also unsuccessful with a perfluoroalkyl-substituted olefin (2z), which underwent exclusive allylic C-H insertion (2z'), highlighting the continued need for catalysts that are able to override substrate control.