Regio- and stereospecific ring opening of 1,1-dialkyl-2- (aryloxymethyl)aziridinium salts by bromide

M. D'Hooghe, V. Van Speybroeck, M. Waroquier, N. De Kimpe
Chemical Communications
14, 1554 -1556


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