| EPSRC Reference: |
GR/T27051/01 |
| Title: |
Organocatalysts in Asymmetric Reactions Mediated Silicon Reagents |
| Principal Investigator: |
Kocovsky, Professor P |
| Other Investigators: |
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| Researcher Co-Investigators: |
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| Project Partners: |
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| Department: |
School of Chemistry |
| Organisation: |
University of Glasgow |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
30 September 2005 |
Ends: |
29 September 2008 |
Value (£): |
303,503
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| EPSRC Research Topic Classifications: |
| Catalysis & Applied Catalysis |
Chemical Synthetic Methodology |
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| EPSRC Industrial Sector Classifications: |
| Environment |
Pharmaceuticals and Biotechnology |
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| Related Grants: |
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| Panel History: |
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Summary on Grant Application Form |
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New, metal-free organocatalysts will be developed for asymmetric reactions employing environmentally friendly silicon reagents. This research will be based on our recent discovery that chiral pyridine-derived N-oxides can be used as very efficient, Lewis-basic catalysts in Sakurai-Hosomi allylation of aldehydes, with the highest enantioselectivity reported to date (98% ee). These catalysts can be synthesised at low cost from the chiral pool in four steps, and can be made available in both enantiomeric forms. The stereochemical architecture, electronic tuning, and mode of action of these catalysts will be investigated in detail both experimentally and by theoretical methods. The scope of the Sakurai-Hosomi reaction is expected to be broadened to heterocyclic and non-aromatic aldehydes; expansion to imines and other electrophiles will be attempted. Other silicon-mediated reactions, such as the asymmetric Mukaiama-aldol condensation, will also be investigated in order to develop new, highly enantioselective, and environmentally benign protocols, applicable in pharmaceutical industry. The most promising catalyst will be anchored to a polymeric support, which should increase their environmental acceptability. The new methodology will be applied in target synthesis, some of which are of direct interest to industry.
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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.gla.ac.uk |