LEWIS-ACID INDUCED REARRANGEMENT OF 2,3-EPOXY AMINES - CHARACTERIZATION OF AZIRIDINIUM ION INTERMEDIATES AND REGIOSPECIFIC RING-OPENING WITH NITROGEN NUCLEOPHILES

Authors
LIU QY SIMMS MJ BODEN N RAYNER CM
Citation
Qy. Liu et al., LEWIS-ACID INDUCED REARRANGEMENT OF 2,3-EPOXY AMINES - CHARACTERIZATION OF AZIRIDINIUM ION INTERMEDIATES AND REGIOSPECIFIC RING-OPENING WITH NITROGEN NUCLEOPHILES, Journal of the Chemical Society. Perkin transactions. I, (11), 1994, pp. 1363-1365
Citations number
38
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
11
Year of publication
1994
Pages
1363 - 1365
Database
ISI
SICI code
0300-922X(1994):11<1363:LIRO2A>2.0.ZU;2-X
Abstract
The Lewis acid induced isomerisation of 2,3-epoxy amines into the corr esponding 2-trimethylsiloxymethylaziridinium ions is described; such i ntermediates have been characterised by H-1 NMR spectroscopy, and reac t with nitrogen nucleophiles regiospecifically to form 1-substituted 2 ,3-diamino alcohols in good to excellent yields and with full stereoch emical control.