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Details of Grant 

EPSRC Reference: GR/L93171/01
Title: 2+2 CYCLOADDITIONS: ACCESS TO NOVEL SCAFFOLDS FOR SOLID-PHASE SYNTHESIS
Principal Investigator: Brown, Professor RCD
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Sch of Chemistry
Organisation: University of Southampton
Scheme: Standard Research (Pre-FEC)
Starts: 01 October 1998 Ends: 30 September 2001 Value (£): 51,883
EPSRC Research Topic Classifications:
Combinatorial Chemistry
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors
Related Grants:
Panel History:  
Summary on Grant Application Form
We have demonstrated that solid-phase [2+2] cycloadditions of keteniminium salts with resin-bound olefins proceed efficiently, using an ester linker. Further work is required to expand the scope of the reaction by the development of alternative linker strategies. The use of a range of new silicon, and ortho-nitrobenzyl linkers will be studied, and their stability to the [2+2] reaction conditions will be assessed. These linkers are considered particularly suitable due to mild cleavage conditions and broad reagent compatibility.We will establish the scope of the solid-phase cycloaddition reaction with respect to olefin and keteniminium substitution, investigating a range of alkyl, heteroatomic, aromatic and heterocyclic substituents.Elaboration of the resin-bound cyclobutanone and cyclobutanone imine adducts will then be studied. Known solution-phase reactions such as carbonyl addition and ring expansion will be applied to the four-membered ring compounds to provide a diverse set of structural templates. Combination of the newly developed linkers, knowledge regarding the scope of the cycloaddition and further transformations of the resin-bound cycloadducts will set the stage for the solid-phase synthesis of novel compounds related to a variety of pharmacologically active targets.
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Organisation Website: http://www.soton.ac.uk