| EPSRC Reference: |
GR/K57053/01 |
| Title: |
SYNTHESIS AND RETRO - COPE CYCLISATIONS OF ALKENYL HYDROXYLAMINES LEADING TO HOMOCHIRAL PYRROLIDINES |
| Principal Investigator: |
Knight, Professor D |
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| Department: |
Chemistry |
| Organisation: |
Cardiff University |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
14 November 1995 |
Ends: |
13 April 1999 |
Value (£): |
141,029
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| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
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Summary on Grant Application Form |
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The central theme will be to thoroughly investigate the scope, limitations and stereochemical features of the retro-Cope reaction of 4-alkenyl-hydroxylamines leading initially to pyrrolidine-N-oxides or N-hydroxypyrrolidines and thence to pyrrolidines. The hydroxylamines will be prepared in homochiral forms from homochiral aldehydes by oxime reduction in appropriate cases, by a novel application of the Mitsunobu reaction and by the coupling of chiral sulphoxide carbanions or enolates with nitrones. The latter chemistry will also be used for the preparation of a variety of homochiral non-natural amino-acids and derivatives. Model studies will establish a predictive transition state for the retro-Cope reaction which will subsequently be applied to the design of target syntheses; specific examples, all chosen to illustrate extensions of the retro-Cope reaction including the pyrrolidine Hygroline, pyrrolizidines, the aspidosperma alkaloid Ibophllidine and Securinine. The viability of the latter two synthetic schemes will be ascertained using model reactions which will be of use in related areas. This chemistry will also provide the first general approach to homoechiral pyrrolidine-N-oxides.
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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.cf.ac.uk |