The reaction conditions identified in entry 11 were assessed for generality by application towards the synthesis of a range of vicinal chloroamines (Scheme 2a). Broad variation of the aniline nucleophile was generally accommodated, delivering the expected chloroamines in good yield and with high enantioselectivity throughout; however, 17 was noted as a clear exception, providing racemic product, which could be related to the pKa of this specific aniline. Confirmation of product stereochemistry was achieved by crystallization of 20, which also highlighted the solid-state conformational preferences of the chloroamine, where the C-Cl is gauche to both nitrogen atoms. Variation of the azaheterocycle was also generally successful (26-35), although significant variation in reactivity was noted and driven by changes in heteroaryl electronics. Other N-nucleophiles (e.g., alkyl amines) were not tolerated in this process due to competing protonation events.