| EPSRC Reference: |
GR/M96841/01 |
| Title: |
CATALYTIC ENANTIOSELECTIVE ALLYLIC AND PROPARGYLIC OXIDATION REACTIONS |
| Principal Investigator: |
Clark, Professor J |
| Other Investigators: |
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| Department: |
Sch of Chemistry |
| Organisation: |
University of Nottingham |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
21 August 2000 |
Ends: |
20 August 2003 |
Value (£): |
170,904
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| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
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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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Simple achiral cyclic alkenes can be converted into alcohol derivatives with -80%ee by direct catalytic acyloxylation. However, it is not possible to achieve high levels of enantiocontrol upon oxidation of cyclic substrates using current catalysts nor to apply the reaction to acyclic alkenes. The objective of the proposed research is the discovery of new chiral copper catalysts that will allow us to prepare allylic alcohol derivatives in a highly enantioselective manner, and the application of the oxidation reaction in several new contexts. In particular, we intend to convert racemic bridged bicyclic alkenes into non-racemic allylic alcohols by a novel symmetrisation-desymmetrisation variant of the reaction. The bicyclic products will serve as useful intermediates and will allow general access to a wide variety of carbocyclic and heterocyclic intermediates. We have demonstrated that it is possible to perform direct enantioselective acyloxylation of alkynes to give esters of propargylic alcohols. The reaction is regioselective and the products can be transformed into a variety of other compounds. We intend to use the propargylic oxidative reaction in an iterative fashion for the preparation polyhydroxylated compounds. In addition, we will explore the efficient synthesis of polyhydroxylated compounds by simultaneous double two-directional oxidation of diynes.
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Key Findings |
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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 |
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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.nottingham.ac.uk |