Lewis acid induced rearrangement of 2,3-epoxy amines; characterisation of aziridinium ion intermediates and regiospecific ring opening with nitrogen nucleophiles
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1363-1365
- https://doi.org/10.1039/p19940001363
Abstract
The Lewis acid induced isomerisation of 2,3-epoxy amines into the corresponding 2-trimethylsiloxymethylaziridinium ions is described; such intermediates have been characterised by 1H NMR spectroscopy, and react with nitrogen nucleophiles regiospecifically to form 1-substituted 2, 3-diamino alcohols in good to excellent yields and with full stereochemical control.Keywords
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