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 language | English |
---|---|
Pages (from-to) | 1563-1568 |
Number of pages | 6 |
Journal | Tetrahedron: Asymmetry |
Volume | 21 |
Issue number | 11-12 |
DOIs | |
Publication status | Published - 23 Jun 2010 |