| EPSRC Reference: |
GR/L94635/01 |
| Title: |
THE DEVELOPMENT OF THE AZA-2,3-WITTIG SIGMATROPIC REARRANGEMENT |
| Principal Investigator: |
Anderson, Professor JC |
| Other Investigators: |
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| Department: |
Unknown |
| Organisation: |
University of Sheffield |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 September 1998 |
Ends: |
30 June 1999 |
Value (£): |
48,241
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| No relevance to Underpinning Sectors |
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Summary on Grant Application Form |
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There is currently a great need by the chemical industry and academic for reliable methods for the stereocontrolled synthesis of nitrogen containing molecules, especially amino acids. We have pioneered the aza-[2, 3]-Wittig sigmatropic rearrangement into a general, high yielding and disastereoselective and widen the reaction scope.Chiral anion chemistry will be developed to dictate the stereoselection of this sigmatropic process; chiral auxiliaries will also be investigated. We plan to investigate more adventurous substrates that will undergo this rearrangement, using cyclopropanes as olefin surrogates and enol ethers and enamines as alkene portions of the rearrangement precursors. The results will be of general importance due to the chiral amines, pyrollidines, piperidines, amino alcohols and diamines that could be prepared, but we see the greatest use of this methodology for the synthesis of unnatural alpha- and beta-amino acids. Unnatural amino acid building blocks can affect the conformations of peptides, often with beneficial results. The development of methodology for the predictable synthesis of multigram quantities of unusual amino acids underpins studies by ourselves and others concerned with the de novo design of peptides.
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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.shef.ac.uk |