Manganese-catalyzed aziridination of olefins with chloramine-T in water and buffered aqueous solutions

A water-soluble, manganese-porphyrin complex was used to catalytically generate aziridines from olefins in moderate to good yields (up to 93%) upon optimization at room temperature and in aqueous media. Reactions using chloramine-T at slightly acidic to neutral pH values showed generally higher catalytic yields. Attempts to integrate this catalytic system into a DNA hybrid catalyst system to support asymmetric aziridination showed little promise, where steric bulk in the axial positions from activation of chloramine-T by this Mn-heme complex may influence its ability to associate with double-stranded DNA. [Display omitted] •Mn-TMPyP4 can utilize chloramine-T as an effective nitrene source to produce aziridines in water and buffered aqueous media.•[Mn(TMPyP4)]I5 complex was used as the catalyst for aziridination with moderate to good yields with a range of olefins.•Addition of several different DNA samples as a chiral auxiliary did not result in enantioselective aziridination.