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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, 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.

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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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