| EPSRC Reference: |
GR/K84882/01 |
| Title: |
CONCISE,FLEXIBLE ROUTES TO CYCLIC DIFLUOROKETONES |
| Principal Investigator: |
Percy, Professor JM |
| Other Investigators: |
|
| Researcher Co-Investigators: |
|
| Project Partners: |
|
| Department: |
School of Chemistry |
| Organisation: |
University of Birmingham |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
02 February 1998 |
Ends: |
01 August 2001 |
Value (£): |
47,124
|
| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
|
|
| EPSRC Industrial Sector Classifications: |
|
| Related Grants: |
|
| Panel History: |
|
|
Summary on Grant Application Form |
|
The addition of a metallated difluoroenol carbamate to an alpha- (carbamoyloxy) -alpha, beta-unsaturated aldehyde followed by a transacylation reaction sets the stage for ring closure via an intramolecular aldol reaction. The cyclopentanone products that obtain will be manipulated via SmI2-mediated reduction and dehydration. Varying the order of these reactions allow three families of useful difluorocyclopentanones to be accessed. The addition a metallated difluoroenol carbamate to an iododifluoromethyl ketone. Cyclisation of these compounds is anticipated under the influence of palladium catalysts. We propose to determine the optimum reaction conditions for a range of substrates and the interaction between ring size and regioselectivity. The knowledge gained will be deployed in an illustrative synthesis of a carbanucleoside. Difluoroenoxy silanes containing a masked carbonyl group will be synthesised and exposed to Lewis acids to develop a Mukaiyama aldol route to medium ring cyclic difluoroketones.
|
|
Key Findings |
|
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
|
|
Potential use in non-academic contexts |
|
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
|
|
Impacts |
|
| Description |
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk |
| Summary |
|
| Date Materialised |
|
|
|
|
Sectors submitted by the Researcher |
|
This information can now be found on Gateway to Research (GtR) http://gtr.rcuk.ac.uk
|
| Project URL: |
|
| Further Information: |
|
| Organisation Website: |
http://www.bham.ac.uk |