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 ANALOGS WITH POTENTIAL GLUCOSYLCERAMIDE SYNTHASE INHIBITORY ACTIVITY

The Lewis acid induced rearrangement of 2,3-epoxy amines into the corr esponding 2-trimethylsilyloxymethylaziridinium ions is described, Such intermediates have been characterised by H-1 NMR spectroscopy, and re act with nitrogen nucleophiles regiospecifically to form 1-substituted 2,3-amino alcohols in good to excellent yields and with full stereoch emical control, This methodology has been applied to the synthesis of a potential inhibitor of glucosylceramide synthase, a promising target for cancer chemotherapy.