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Details of Grant 

EPSRC Reference: GR/N24384/01
Title: SILENES: NOVEL SYNTHETIC REAGENTS FOR OLEFIN FUNCTIONALISATION
Principal Investigator: Steel, Professor P
Other Investigators:
Researcher Co-Investigators:
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Department: Chemistry
Organisation: Durham, University of
Scheme: Standard Research (Pre-FEC)
Starts: 01 October 2001 Ends: 30 September 2004 Value (£): 80,360
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
Chemicals Pharmaceuticals and Biotechnology
No relevance to Underpinning Sectors
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Summary on Grant Application Form
This proposal is concerned with the development of methods for the stereocontrolled functionalisation of (-bonded systems through the reaction with readily accessible silenes and the subsequent elaboration of the resultant adducts. More specifically we intend to explore a range of structurally diverse silenes and alkene components in order to probe the diastereoselectivity obtainable with both 4( (Diels Alder reactions, both inter- and intramolecular, with dienes, unsaturated carbonyl compounds etc.) and 2( components ([2+2] cycloaddition reactions). Efforts to develop asymmetric versions (chiral silenes) of these reactions will be undertaken using classical chiral auxiliary strategies.A key aspect of the work is the extrusion of the silicon atom form the cycloadduct via Fleming-Tamao type oxidation to produce highly functionalised molecules with a high degree of stereocontrol. The extension of this latter area to produce the analogous amines will also be explored.Validation of the new methodology will be achieved through the application of this methodology in the synthesis of a number of biologically active structures including nephromopsinic acid and the higher sugar KDO.
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