Abstract
Original language | English |
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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 |
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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; Carbone, Giorgio; Barker, Graeme; O'Brien, Peter; Shipton, Mark R.; Gilday, John; Campos, Kevin R.
In: Tetrahedron: Asymmetry, Vol. 21, No. 11-12, 23.06.2010, p. 1563-1568.Research output: Contribution to journal › Article
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
VL - 21
SP - 1563
EP - 1568
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
SN - 0957-4166
IS - 11-12
ER -