| EPSRC Reference: |
GR/R87444/01 |
| Title: |
Intramolecular Diels-Alder Reactions of Tethered furan DEAD derivations |
| Principal Investigator: |
Bew, Dr S |
| Other Investigators: |
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| Researcher Co-Investigators: |
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| Department: |
Chemistry |
| Organisation: |
University of East Anglia |
| Scheme: |
Fast Stream |
| Starts: |
01 October 2002 |
Ends: |
30 September 2005 |
Value (£): |
63,527
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| EPSRC Research Topic Classifications: |
| Asymmetric Chemistry |
Chemical Synthetic Methodology |
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| EPSRC Industrial Sector Classifications: |
| Pharmaceuticals and Biotechnology |
No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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The intramolecular Diels-Alder reaction is widely used as a strategy for the synthesis of cyclic ring systems with high regio- and stereocontrol. The possibility that novel spiro-amide ring systems could be synthesised in an asymmetric process via an IMDA reaction using furan and an azo species joined via a tether equipped with stereogenic centres is intriguing. The proposed research programme aims to investigate the effect that changing the position, the type and the electronic character of the stereogenic substituents on the tether will have on the yield and facial selectivity within the IMDA reaction. Subsequent reductive hydrogenation is expected to cleave the N-N bond resulting in a novel spiro-amide species. The spiro-amides possess an allyl amine within their structure which may be amenable to the synthesis of a (pi-allyl)palladium species and subsequent reaction with nudeophiles. This investigation will focus on the regio- and stereoseledivity of the nudeophile addition. Having completed a comprehensive study on the reactivity and conformational aspects of the spiro-amide system the methodology will be extended (if time allows) to undertake the synthesis of biologically interesting natural product analogues.
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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.uea.ac.uk |