| EPSRC Reference: |
GR/S90959/01 |
| Title: |
Enantioselective synthesis of chiral carbenoids via asymmetric halogen-metal exhange |
| Principal Investigator: |
Blakemore, Dr P |
| Other Investigators: |
|
| Researcher Co-Investigators: |
|
| Project Partners: |
|
| Department: |
Sch of Chemistry |
| Organisation: |
University of Leeds |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 October 2004 |
Ends: |
30 September 2007 |
Value (£): |
75,726
|
| EPSRC Research Topic Classifications: |
| Chemical Synthetic Methodology |
|
|
| EPSRC Industrial Sector Classifications: |
| Chemicals |
Pharmaceuticals and Biotechnology |
|
| Related Grants: |
|
| Panel History: |
|
|
Summary on Grant Application Form |
|
Recent studies by Hoffmann and co-workers have established that alpha-haloalkylmagnesium reagents exhibit exceptional chemical and configurational stability. A multitude of useful applications for this class of chiral carbenoids can be readily envisioned; however, the inefficiency of methods currently available for the enantioselective preparation of alpha-haloalkylmetal species severely detracts from the utility of these valuable reagents. The aim of the proposed research is to develop an asymmetric halogen metal exchange (AHME) process to generate enantioenriched alpha-iodoalkylmagnesium reagents directly from readily available 1,1 -diiodoalkanes by iodine-magnesium interchange. Discrimination of the enantiotopic iodine atoms within geminal diiodides will be effected by suitably engineered chiral organomagnesium reagents based on a planar chiral ferrocenyl scaffold. The AHME reagents will themselves be generated by an iodine-magnesium interchange process thus opening the possibility for reagent precursor recycling or even a catalytic variant of AHME. The stereoselectivity of the AHME process will be probed indirectly by reacting the in situ generated chiral carbenoids with aldehydes and determining enantiomeric excess for the resultant epoxides/halohydrins. An enantioselective synthesis of alpha-beta-epoxysilanes via AHME on (diiodomethyl)trimethylsilane followed by carbonyl addition will also be investigated.
|
|
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.leeds.ac.uk |