| EPSRC Reference: |
GR/K80419/01 |
| Title: |
CATALYTIC ASYMMETRIC BAYLIS-HILLMAN REACTIONS. |
| Principal Investigator: |
Barrett, Professor T |
| Other Investigators: |
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| Project Partners: |
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| Department: |
Chemistry |
| Organisation: |
Imperial College London |
| Scheme: |
LINK |
| Starts: |
01 October 1995 |
Ends: |
30 November 1998 |
Value (£): |
60,996
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| EPSRC Research Topic Classifications: |
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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 objectives of this research are to deveopp novel catalysts for the efficient production of *-methylene secondary alcohols in high optical purity using the Baylis-Hillman reaction. The methods will subsequently be applied for the stereocontrolled synthesis of derived Michael adducts, aldols, vicinal diols, amino acids and related fine chemicals using environmentally friendly protocols. Two distinct procedures for enantioselective catalysis will be explored: (1) the use of chiral pyrrolizidine and azetidine derivatives as surrogates for DABCO and (2) the use of trimethylsilyl sulfides, selenides and halides with tartrate borane Lewis acid additives. A series of Michael acceptors will be allowed to react with aldehydes in the presence of chiral pyrrolizidines and azetidine derivatives to provide *-hydroxy*-methylene esters, nitriles and ketones. Secondly, chiral borane Lewis acids will be used to catalyse the condensation of trimethylsilyl sulfides, selenides and halides with Michael acceptors and aldehydes to provide enantiomerically enriched Baylis-Hillman adducts. The influence of catalyst, aledhyde and Michael acceptor structure on enantioselectivities in both procedures will be determined and the efficiency of reactions optimised.
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Key Findings |
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Potential use in non-academic contexts |
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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.imperial.ac.uk |