Projects per year
Abstract
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. (C) 2010 Elsevier Ltd. All rights reserved.
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 |
Keywords
- OPTICALLY-ACTIVE 3-HYDROXYPIPERIDINES
- EFFICIENT SYNTHESIS
- (+)-SPARTEINE SURROGATE
- SUBSTITUTED STYRENES
- ALPHA-MANNOSIDASE
- CHIRAL DIAMINES
- AMINOHYDROXYLATION
- EXPANSION
- REARRANGEMENT
- SWAINSONINE
Projects
- 1 Finished
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Back to Basics: Investigating Structure,reactivity and catalysis of organlithium diamine complexes
O'Brien, P. A. (Principal investigator), Hilmersson, G. (Researcher) & Carbone, G. (Student)
1/10/07 → 31/03/11
Project: Research project (funded) › Research