| EPSRC Reference: |
GR/S04635/01 |
| Title: |
Stereoselective Oxy-Michael Reactions of Delta-Lactol Anions: New Methodology and Synthetic Applications |
| Principal Investigator: |
Dixon, Professor DJ |
| Other Investigators: |
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| Project Partners: |
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| Department: |
Chemistry |
| Organisation: |
University of Cambridge |
| Scheme: |
First Grant Scheme Pre-FEC |
| Starts: |
01 April 2003 |
Ends: |
31 August 2004 |
Value (£): |
102,562
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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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Treatment of the potassium salts of enantiopure 6-substituted lactols with crown ethers followed by beta-substituted nitro-olefins in THF at -78C affords the Oxy-Michael adducts in good yields (+80%) and excellent diastereoselectivities (95-98% de). This reaction is clearly of immediate synthetic utility as the products may be transformed into a range of desirable structural motifs. We wish to explore further the scope of this reaction and to assess which Michael acceptors are suitable substrates in the reactions and if the high levels of diastereocontrol witnessed in the preliminary results transfer to other substrates. In addition, the anionic Michael adducts are still nucleophilic and we wish to explore the stereocontrol possible in tandem Oxy-Michael /alkylations and OxyMichael/Henry reactions. When a clearer picture of the scope is formed, we wish to apply the results to the synthesis of a range of bioactive natural products and pharmaceutical targets. Here, the Oxy-Michael reaction will constitute the key stereocontrolling step and the product materials will include enantiopure substituted 1,2-aminoalcohols, tetrahydroisoquinolines, C2-symmetric alkaloids.
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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.cam.ac.uk |