Stereospecific aziridination of olefins via electrophile-induced cyclization of gamma,delta-unsaturated imines and subsequent hydrolytic rearrangement.
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.
D'hooghe
Matthias
M
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium.
Boelens
Mark
M
Piqueur
Johan
J
De Kimpe
Norbert
N
D000475:Alkenes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D006868:Hydrolysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D001388:Aziridines; D007097:Imines