| EPSRC Reference: |
GR/M13633/02 |
| Title: |
ASYMMETRIC MAGNESIUM-BASED CATALYSTS FOR ADDITION REACTIONS |
| Principal Investigator: |
Jackson, Professor R |
| Other Investigators: |
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| Project Partners: |
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| Department: |
Chemistry |
| Organisation: |
University of Sheffield |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 January 2001 |
Ends: |
30 April 2002 |
Value (£): |
70,332
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| EPSRC Research Topic Classifications: |
| Catalysis & Applied Catalysis |
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| EPSRC Industrial Sector Classifications: |
| Pharmaceuticals and Biotechnology |
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Summary on Grant Application Form |
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The aim of this project is to develop novel catalysts for a series of addition reactions of stabilised nucleophiles (malonate derivatives, nitroalkanes) to electron-deficient alkenes and aldehydes. The basis of our approach is our recent discovery that a material obtained by treatment of dibutylmagnesium with diethyl tartrateis capable of catalysing the nucleophilic epoxidation of enones using tert-butyl hydroperoxide with good to excellent enantiomeric excess (80-95% ee). The key part of this process is a nucleophilic attack by tert-butyl hydroperoxide on the enone.We believe that the active catalyst is a magnesium bis-alkoxide, which functions both as base (to activate the tert-butyl hydroperoxide by deprotonation) and as a Lewis acid (to activate the enone by complexation). We will attempt to characterise the catalyst so as to be able to design more effective catalytic compounds. We then wish to attempted these new catalysts to a series of addition reactions, which should all be amenable to catalysis by a species that is both a base and a Lewis acid. The target reactions include the catalytic asymmetric addition of stabilised carbanions to enones, and of nitroalkanes to electron-deficient alkenes and aldehydes. The preparation of polymer-supported analogues of these catalysts will also be addressed.
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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.shef.ac.uk |