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Details of Grant 

EPSRC Reference: GR/L63167/01
Title: THE DIRECTED DIHYDROXYLATION OF FUNCTIONALISED ALKENES
Principal Investigator: Donohoe, Professor T
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Evotec (UK) Ltd Johnson Matthey Lancaster Synthesis Ltd
Department: Chemistry
Organisation: Victoria University of Manchester, The
Scheme: Standard Research (Pre-FEC)
Starts: 27 October 1997 Ends: 26 October 2000 Value (£): 148,927
EPSRC Research Topic Classifications:
Asymmetric Chemistry
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors
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Panel History:  
Summary on Grant Application Form
The programme is designed to investigate and exploit a novel oxidation system that we have discovered recently. The combination of osmium tetraoxide and TMEDA has been shown to allow the directed dihydroxylation of functionalised alkenes, using hydrogen-bonding as a control element. This is an interesting new reaction, and we aim to explore its scope and prepare sterochemically defined triols and tetraols in a manner that was previously unknown. Both cyclic and acylic systems will be investigated, together with homoallylic alcohols and sulfonamides.We then aim to use this new chemistry to enable the synthesis of biologically important compounds in a novel and particularly concise manner: targets are mannostatin and the cyclopentane moiety of funiculosin.In addition, the application of some inorganic chemistry should enable us to understand and improve upon this new oxidising reagent, with the ultimate aim of developing a catalytic process for the syn selective dihydroxylation of functionalised alkenes. We would also like to use this methodology to develop a simple test for the ligand acceleration effect.
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