| EPSRC Reference: |
GR/M70964/01 |
| Title: |
A RADICAL STEREOCONTROLLED SYNTHESIS OF PIPERIDINES |
| Principal Investigator: |
Snaith, Dr J |
| Other Investigators: |
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| Project Partners: |
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| Department: |
School of Chemistry |
| Organisation: |
University of Birmingham |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 1999 |
Ends: |
30 September 2002 |
Value (£): |
52,632
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| EPSRC Research Topic Classifications: |
| Biological & Medicinal Chem. |
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| EPSRC Industrial Sector Classifications: |
| 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 synthesise piperidines by the 6-exo-trig cyclisation of a free-radical onto an appropriately activated double bond. Piperidines are of considerable interest, occurring in an enormous array of biologically-active natural products and pharmaceuticals. Amino acids from the chiral pool will provide the source of chirality, with the single stereogenic centre of the amino acid controlling the formation of new stereogenic centres in the product piperidine. A free-radical approach to piperidines has not been explored before, and offers a number of attractive advantages, key amongst which are the tolerance of a wide range of functionality and the potential to achieve a very high degree of stereocontrol. The amino acid stereogenic centre will become C-2 of the new piperidine, and will control the stereochemistry at C-4 as the C-3 to C-4 bond is formed. Closure of the ring to afford either a cis or trans disposition between C-2 and C-4 should be possible by varying the substituent on nitrogen. Small substituents on nitrogen will allow both the C-2 and C-4 groups to sit pseudo equatorial in the transition state, leading to the cis piperidine, whilst a bulky, planarising substituent on nitrogen will force C-2 pseudo C-2 pseudo axial, producing the trans piperidine.
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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.bham.ac.uk |