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.
D'hooghe
Matthias
M
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Belgium. norbert.dekimpe@UGent.be
Van Speybroeck
Veronique
V
Waroquier
Michel
M
De Kimpe
Norbert
N
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