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Details of Grant 

EPSRC Reference: GR/M44460/01
Title: NEW DEVELOPMENTS IN RAMBERG-BACKLAND & EPISULFONE CHEMISTRY
Principal Investigator: Taylor, Professor R
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Chemistry
Organisation: University of York
Scheme: Standard Research (Pre-FEC)
Starts: 06 December 1999 Ends: 05 September 2003 Value (£): 155,038
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors Chemicals
Pharmaceuticals and Biotechnology
Related Grants:
Panel History:  
Summary on Grant Application Form
The Ramberg-Backlund rearrangement is a valuable carbon-carbon bond forming reaction but with an inherent disadvantage in that the alpha-halosulfone is converted into an alkene with a net loss of functionality. We have devised the three novel Ramberg-Backlund variants which lead to functionalised alkenic products by virtue of functionality being retained during the rearrangement, being introduced during the rearrangement, or being present in the substrate. These three novel variants proceed by: (I) incorporating the alpha-sulfonyl leaving group into a three membered ring to produce allylic alcohols, amines etc. after rearrangement, (ii) utilising a tandem conjugate addition-Ramberg-Backlund process between alpha-bromovinyl sulfones and heteronucleophiles, (iii) commencing with S-glycoside dioxides and employing the Meyers' modification. In addition, we have developed episulfone deprotonation-trapping procedures to add functionality during a traditional Ramberg-Backlund rearrangement. Preliminary results are presented which attest to the likely success of this proposal. We plan to build on these preliminary studies to determine the scope and limitations of the novel procedures described above. We will then apply this methodology to the synthesis of chiral building blocks and natural products, including the development of versatile new routes to C-glycosides and C-linked disaccharides.
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Organisation Website: http://www.york.ac.uk