| EPSRC Reference: |
GR/N05222/01 |
| Title: |
NITROGEN HETEROCYCLES BY TANDEM CATIONIC CYCLISATION- AZIRIDINIUM ION FORMATION - NUCLEOPHILIC RING OPENING |
| Principal Investigator: |
Rayner, Professor CM |
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| Department: |
Sch of Chemistry |
| Organisation: |
University of Leeds |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 2000 |
Ends: |
30 September 2003 |
Value (£): |
73,227
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| Chemicals |
Pharmaceuticals and Biotechnology |
| No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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This project aims to develop new methods for the stereocontrolled synthesis of a wide range of pyrrolidines and piperidines using a novel tandem cationic cyclisation-aziridinium ion formation-nucleophilic ring opening strategy. Reaction of N-allyl alpha-aminoacetals with a Lewis acid generates an alpha-alkoxyaziridinium ion which when dissolved in a Lewis basic solvent undergoes subsequent rearrangement to a bicyclo(3.1.0)aziridinium species. This intermediate can be isolated, or reacted with nucleophiles to give 1,2,4 -trisubstituted pyrrolidines. Alternative N-substituents should also allow for the synthesis of bicyclo(3.1.0) systems with the aziridine ring still intact, similar to that in azinomycin and related compounds. Initial results indicate that a single diastereoisomer of the product should be formed. A range of substrates will be investigated to determine the generality of the reaction, which will also provide valuable mechanistic information. Substrates derived from optically active N-allylamines will be used for the preparation of optically active heterocycles. The potential of this reaction for the synthesis of piperidines will also be investigated. Subsequently, the chemistry will be transferred to the solid phase for the construction of diverse libraries of heterocyclic compounds. The synthesis of molecules of potential biological activity will be a goal throughout the period of the project.
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Key Findings |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Potential use in non-academic contexts |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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Impacts |
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| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
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| Date Materialised |
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Sectors submitted by the Researcher |
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This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
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| Project URL: |
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| Further Information: |
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| Organisation Website: |
http://www.leeds.ac.uk |