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 β-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 β-chloro intermediate and provide additional insight into the mechan...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-07, Vol.10 (14), p.2655-2663
Main Authors: Anderson, Shelby R., Ayers, Joshua T., DeVries, Keith M., Fumitaka Ito, Mendenhall, Debra, Vanderplas, Brian C.
Format: Article
Language:English
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Summary:Here we describe a one-pot synthesis of a series of β-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 β-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 β-substituted amine products.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00243-8