1213615-72-5Relevant academic research and scientific papers
Asymmetric synthesis via aziridinium ions: Exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (-)-swainsonine
Oxenford, Sally J.,Moore, Stephen P.,Carbone, Giorgio,Barker, Graeme,O'Brien, Peter,Shipton, Mark R.,Gilday, John,Campos, Kevin R.
experimental part, p. 1563 - 1568 (2010/10/20)
The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH 2 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.
