| EPSRC Reference: |
GR/M11073/01 |
| Title: |
ASYMMETRIC SYNTHESIS OF 1,2-AMINO ALCOHOLS THROUGH THE ADDITION OF CHIRAL ALPHA-SILYL ANIONS IMINES |
| Principal Investigator: |
Marsden, Professor SP |
| Other Investigators: |
|
| Researcher Co-Investigators: |
|
| Project Partners: |
|
| Department: |
Chemistry |
| Organisation: |
Imperial College London |
| Scheme: |
Standard Research (Pre-FEC) |
| Starts: |
01 September 1998 |
Ends: |
31 August 2001 |
Value (£): |
50,685
|
| EPSRC Research Topic Classifications: |
|
| EPSRC Industrial Sector Classifications: |
| No relevance to Underpinning Sectors |
|
|
| Related Grants: |
|
| Panel History: |
|
|
Summary on Grant Application Form |
|
A novel two-step, three component asymmetric synthesis of 1, 2-amino alcohols is proposed. These subunits are of vital importance in the pharmaceutical industry (for example as peptidase inhibitors) and to the academic and fine chemical industries as the basis of new ligands for asymmetric catalysis. The new method involves the addition of chiral alpha-silyl anions (generated by addition of organometallic reagents to vinyl silanes) to imines. Oxidative C-Si bond cleavage then furnishes the amino alcohol in just two steps. The chiral directing groups will be chiral pool derived diamines, which are readily coupled with the commercially available chlorodimethylvinylsilane. The effect of diamine structure on both the stability and reactivity of the alpha-silyl anions will be studied, and the information gained to rationally design directing groups to maximise enantio- and diastereoselectivity in the addition step. The flexibility and brevity of the new approach will be demonstrated in the short (four step) synthesis of important 1, 2-amino alcohols such as statine, a key component of the peptidase inhibitor pepstatin.
|
|
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.imperial.ac.uk |