Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine

Sally J. Oxenford, Stephen Moore, Giorgio Carbone, Graeme Barker, Peter O'Brien, Mark R. Shipton, John Gilday, Kevin R. Campos

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via an aziridinium ion) was used to synthesise a piperidine alcohol. In this way, a formal synthesis of (−)-swainsonine was completed.
Original languageEnglish
Pages (from-to)1563-1568
Number of pages6
JournalTetrahedron: Asymmetry
Volume21
Issue number11-12
DOIs
Publication statusPublished - 23 Jun 2010

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