The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate

Here we describe a one-pot synthesis of a series of beta-substituted amines as single enantiomers from an initial regioisomeric mixture of styrene oxide ring-opening products. We also report the isolation and characterization of a key beta-chloro intermediate and provide additional insight into the mechanism of the reported alkylations. These results require that the reaction proceeds through a common aziridinium ion intermediate on two separate occasions in order to account for the observed overall net retention of configuration in proceeding from (S)-styrene oxide to the desired beta-substituted amine products. (C) 1999 Elsevier Science Ltd. All rights reserved.