J. Aires-de-Sousa, S. Prabhakar, A. M. Lobo, A. M. Rosa, M. J. S. Gomes, M. C. Corvo, D. J. Williams, and A. J. P. White
“Chiral Synthesis of N-Aryl Aziridines”
Tetrahedron: Asymmetry2001, 12 (24), 3349-3365.

Abstract

The reaction of a variety of N-arylhydroxamates as the nitrogen transfer reagent to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer’s sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer’s auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenyl aziridine-2-carboxylate. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with chiral quaternary salts based on cinchona alkaloids especially with that of cinchonine. A model is presented to explain the origin of enantioselection and a mechanism proposed for the aziridination reaction.