Generation of homochiral aziridinium ion intermediates derived from 2,3-epoxy amines: regiospecific nucleophilic trapping with nitrogen nucleophiles. Application in the synthesis of novel morpholinosphingolipid analogues with potential glucosylceramide synthase inhibitory activity
- 1 January 1997
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 511-526
- https://doi.org/10.1039/a604534k
Abstract
The Lewis acid induced rearrangement of 2,3-epoxy amines into the corresponding 2-trimethylsilyloxymethylaziridinium ions is described. Such intermediates have been characterised by 1H NMR spectroscopy, and react with nitrogen nucleophiles regiospecifically to form 1-substituted 2,3-amino alcohols in good to excellent yields and with full stereochemical control. This methodology has been applied to the synthesis of a potential inhibitor of glucosylceramide synthase, a promising target for cancer chemotherapy.Keywords
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