The presence of nitrogen functional groups in pharmaceuticals, agrochemicals, and natural products is essential to their beneficial physiochemical and biological properties. This importance of the carbon-nitrogen bond has long inspired organic chemists to devise new methods for expedited and precise installation of nitrogen into compounds, advancements with significant potential to contribute to the identification and expansion of new chemical space. Toward this goal, transition metal-catalyzed nitrene transfer (NT) has emerged as an elegant strategy that directly transforms ubiquitous structural moieties, including olefins and C-H bonds, into valuable nitrogen-containing building blocks. Chief among these are aziridines, resulting from nitrene insertions into alkenes, which are well-known for their frequent occurrence in natural products and bioactive molecules, as well as their synthetic utility. The reactivity of these smallest N-heterocycles is mainly attributed to their strained nature that leads to a high propensity to undergo ring-opening and ring-expansion processes, often with excellent regiocontrol and stereochemical integrity of the newly created stereogenic center(s). Therefore, aziridines are exceptionally versatile and efficient intermediates for olefin difunctionalization, as well as the construction of higher-order heterocyclic scaffolds that feature prominently among medicinal chemists' most desirable synthetic targets. Due to the potential of alkene aziridination to introduce structural and stereochemical complexity from feedstock starting materials, the development of enantioselective aziridination strategies via NT is of key importance in organic synthesis. Early work by Evans and Jacobsen reported asymmetric intermolecular aziridinations with copper salts supported by chiral bis(oxazoline) (BOX) and chiral diamine-based ligands , respectively (Scheme 1A). Although satisfactory yields and ee were observed with only a few select substrates, these results stimulated the discovery of several catalytic systems for both asymmetric inter-and intramolecular aziridinations that employ a variety of other metals, ligand scaffolds, and nitrene precursors. Despite remarkable advances in both generality and efficiency, most of these methods, especially for intermolecular reactions, give the best results for terminal, styrene-based, and other conjugated olefins. In contrast, intramolecular aziridinations via NT exhibit superior reactivity and stereoselectivity with internal and unactivated olefins, yet have received much less attention (Scheme 1B). In 2003, Che developed a chiral dirhodium complex to catalyze intramolecular aziridination of alkenes with sulfonamides and carbamates in up to 76% ee. Dauban later used a copper-BOX complex to afford the intramolecular aziridination of sulfamates in up to 84% ee, although substrates bearing unconjugated or terminal olefins gave less satisfactory results. In 2017, Zhang used an alternative strategy to iminoiodinane-based nitrene formation, reporting enantioselective aziridinations with allyl azidoformates via a radical pathway catalyzed by a cobalt-porphyrin complex. This catalyst gave excellent enantioselectivity when substrates containing (E)-olefins