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

Abstract

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.

Keywords

• Manganese
• Catalysis
• Aziridination
• TMPyP4
• Chloramine-T
• Nitrene transfer