Aziridines are valuable strained three-membered nitrogen containing heterocycles known for their utility as nitrogen building blocks. Chiral aziridines command an elevated level of interest as they serve as excellent chiral building blocks and intermediates for the stereoselective incorporation of nitrogen while allowing for downstream diversification through regio-and stereoselective opening of the strained ring. Nucleophilic ring opening with or without Lewis acid activation is the most frequently employed method for aziridine diversification and can afford access to chiral amines, amino alcohols, amino acids, and other chiral nitrogen motifs. The ease with which chiral aziridines can be diversified has made them desirable targets and has driven the development of synthetic methods to access them in an expedient fashion. Stereoselective synthesis of aziridines can be achieved through three distinct synthetic disconnections: 1) intramolecular condensation of chiral halo-amines or amino alcohols, 2) stereoselective addition of carbon sources to imines, or 3) stereoselective addition of nitrene equivalents to alkenes. Of these, the addition of a nitrene equivalent across an alkene is the most attractive, due to the simplicity of the disconnection and the availability of alkene building blocks. While catalytic methods have been developed using organocatalysts, transition metal catalyzed methods have remained the predominant means of accessing chiral aziridines through this disconnection. Following seminal work by Evans and Jacobsen, development of Cu(II) catalyzed methodologies have received the most attention using discreet or in situ generated hypervalent imino-iodinane nitrene sources. Since then, other methodologies have been developed using Ru(II), Co(II), Rh(II), Fe(II), Mn(III), and Ag(I), along with a variety of unique ligand designs and nitrene sources, enabling both intra-and intermolecular stereoselective aziridinations. However, these methods have focused on the aziridination of activated alkenes such as styrenes and α,β-unsaturated systems (Scheme 1a, top). The stereoselective aziridination of unactivated alkenes with alkyl substitutions remains challenging (Scheme 1a, bottom). As a result, only four methods that are capable of conducting intermolecular enantioselective aziridinations on unactivated alkenes have been reported. A Co(II) porphyrin catalyst developed by Zhang was shown to aziridinate a variety of styrenyl substrates along with a small number of unactivated substrates. A report by Katuski using a Ru(II)[salen] catalyst also showed the aziridination of a small number of unactivated alkenes alongside activated systems. In 2022, Dauban reported on the asymmetric aziridination of tetra substituted styrenes using a chiral dirhodium(II) tetracarboxylate catalyst and showed that unactivated alkenes could also function in this system. In a recent report, Phipps showed the use of an achiral dirhodium(II) catalyst in conjunction with a chiral cationic organocatalyst and a pendant hydroxyl directing group for the aziridination of both activated and unactivated alkenes with a variety of substitution patterns. These methods represent significant advances in enantioselective aziridination technology, but there still exists room for further development. While each of these methods can conduct aziridinations on unactivated systems, their focus still lies with activated substrates, with unactivated systems often providing lower yields and enantioselectivities. Furthermore, each of these systems relies on either azide or in-situ generated imino-iodinane nitrene sources which can present safety and chemoselectivity liabilities.