| EPSRC Reference: |
GR/L58439/01 |
| Title: |
CHIRAL BASE-MEDIATED DESYMMETRISATION REACTIONS: SYNTHESIS OF PSEUDO-SUGARS,AZASUGARS AND AMINO ACIDS |
| Principal Investigator: |
O'Brien, Professor P |
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| Department: |
Chemistry |
| Organisation: |
University of York |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 1997 |
Ends: |
30 September 2000 |
Value (£): |
49,141
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| No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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Epoxides can be converted into enantiomerically enriched allylic alcohols using chiral bases. When the epoxide is a substituted meso cyclohexene oxide , the reaction is termed asymmetric desymmetrisation and highly functionalised cyclohexene oxide, the reaction is termed asymmetric desymmetrisation and highly functionalised cyclohexane products are obtained. By rearranging single diastereomers of meso epoxides with chiral bases, we and others have shown that it is possible to totally control the relative and absolute stereochemistry of allylic alcohols. Thus, chiral base-mediated desymmetrisation is an extremely powerful tool in asymmetric synthesis and thus merits further investigation evaluation. This proposal describes how we will rearrange some new meso epoxides (aziridine and diamino epoxides) and then use the allylic alcohol products in the synthesis of some pseudo-sugars, azasugars and amino acids which may possess glycosidase inhibition and antibiotic properties. One of the key aspects of this project is that ability to selectivity prepare all 8 possible stereolsomers of a given pseudo-sugar, azasugar or amino acid. This will be particularly useful for biological evaluation.Key features of our proposed study are : (1) development of stereoselective routes to each of the epoxide diastereomers; (2) detailed investigation of new chiral base-mediated epoxide rearrangement reactions; (3) use of allylic alcohols in the preparation of biologically interesting cyclic and acyclic compounds.
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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 |
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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.york.ac.uk |