Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultam

Cantrill, Alex A. and Hall, Lee D. and Jarvis, Ashley N. and Osborn, Helen M.I. and Raphy, Jenny and Sweeney, J. B. (1996) Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultam. Chemical Communications, 1996 (23). pp. 2631-2632. ISSN 1359-7345

Abstract

The aza-Darzens reaction of the chiral enolate derived from bromoacetylcamphorsultam 1 with N-(diphenylphosphinyl)aryl- and tert-butyl-methanimines proceeds in good yield to give cis-N-(diphenylphosphinyl)aziridinylcarbonyl sultams with high de. Monochiral cis-aziridinecarboxylates may be obtained in acceptable yield by hydrolysis of these sultams.