Stereospecific aziridination of olefins via electrophile-induced cyclization of gamma,delta-unsaturated imines and subsequent hydrolytic rearrangement

Chem Commun (Camb). 2007 May 21:(19):1927-9. doi: 10.1039/b703147e.

Abstract

The olefinic bond of gamma,delta-unsaturated aldehydes underwent a net aziridination through electrophile-induced cyclization and subsequent rearrangement of the resulting cyclic iminium salts: this methodology allows the stereospecific introduction of aziridine moieties into cyclic systems.

MeSH terms

  • Alkenes / chemistry*
  • Aziridines / chemistry*
  • Cyclization
  • Hydrolysis
  • Imines / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkenes
  • Aziridines
  • Imines