TY - JOUR
T1 - Asymmetric synthesis via aziridinium ions: exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (−)-swainsonine
AU - Oxenford, Sally J.
AU - Moore, Stephen
AU - Carbone, Giorgio
AU - Barker, Graeme
AU - O'Brien, Peter
AU - Shipton, Mark R.
AU - Gilday, John
AU - Campos, Kevin R.
PY - 2010/6/23
Y1 - 2010/6/23
N2 - 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.
AB - 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.
U2 - 10.1016/j.tetasy.2010.03.048
DO - 10.1016/j.tetasy.2010.03.048
M3 - Article
SN - 0957-4166
VL - 21
SP - 1563
EP - 1568
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
IS - 11-12
ER -