Regioselective Ring\nOpening of Aziridines by Oximes\nvia C–C Bond Cleavage: Access to a Library of Oxime-Ethers

A series\nof sulfonamido-substituted oxime-ethers have been synthesized\nby the reaction of donor–acceptor aziridines with aldo- and\nketo-oximes through C–C bond cleavage. Nucleophilic attack\nby an oxime hydroxyl group on the <i>in situ</i>-generated\nazomethine ylide rather than the routine cycloaddition reaction draws\nthe novelty of the developed methodology. Selective protection of\nthe oxime hydroxyl group is observed in the presence of phenolic −OH,\nwhich made the protocol enriched. In terms of a synthetic point of\nview, the uniqueness had been drawn further as it occurred at room\ntemperature and within 30 min. Participation of a wide range of aziridines\nwith a series of aldo- and keto-oximes made the developed methodology\ngeneralized by creating a novel library of substituted oxime-ethers.