Regio- and stereospecific ring opening of 1,1-dialkyl-2-(aryloxymethyl)aziridinium salts by bromide.
Enantiomerically pure 2-(aryloxymethyl)aziridines are efficiently transformed into chiral N-(2-bromo-3-aryloxypropyl)amines via a regio- and stereospecific ring opening of the intermediate aziridinium salts, and the experimental results are rationalized on the basis of some high level ab initio calculations.
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium. norbert.dekimpe@UGent.be
Matthias
M
D'hooghe
Veronique
V
Van Speybroeck
Michel
M
Waroquier
Norbert
N
De Kimpe
D000588:Amines / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry*; D012492:Salts; D013237:Stereoisomerism; D013816:Thermodynamics
D000588:Amines; D001388:Aziridines; D012492:Salts; D001966:Bromine