Previous work within our group sought to access this underexplored chemotype through a chiral phosphoric acid (CPA)-catalyzed enantioselective aza-Michael addition of aromatic amines to chlorovinyl heterocycles, followed by basic annulation (Scheme 1b). This yielded chiral mono-substituted α-heterocyclic aryl aziridines with high yield and ee. A limitation of this approach was the lack of further substitution on the aziridine ring. We therefore sought to expand the scope of this CPA strategy by establishing a method for the synthesis of 1,2disubsituted α-heterocyclic aryl aziridines. Here we provide a full account of this reaction development, including scope, limitations, and mechanism.