Oxenford, SJ;
Moore, SP;
Carbone, G;
Barker, G;
O'Brien, P;
Shipton, MR;
Gilday, J;
(2010)
Asymmetric synthesis via aziridinium ions: Exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (-)-swainsonine.
Tetrahedron Asymmetry
, 21
(11-12)
pp. 1563-1568.
10.1016/j.tetasy.2010.03.048.
Abstract
The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH2as 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. © 2010 Elsevier Ltd. All rights reserved.
| Type: | Article |
|---|---|
| Title: | Asymmetric synthesis via aziridinium ions: Exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (-)-swainsonine |
| DOI: | 10.1016/j.tetasy.2010.03.048 |
| URI: | http://discovery.ucl.ac.uk/id/eprint/1373177 |
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