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Details of Grant 

EPSRC Reference: GR/L04719/01
Title: CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALISED ALKENNES
Principal Investigator: Aggarwal, Professor VK
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Chirotech Technology Limited GlaxoSmithKline plc (GSK) Pfizer
Department: Chemistry
Organisation: University of Sheffield
Scheme: LINK
Starts: 01 May 1996 Ends: 30 April 1999 Value (£): 27,000
EPSRC Research Topic Classifications:
Asymmetric Chemistry
EPSRC Industrial Sector Classifications:
Pharmaceuticals and Biotechnology
Related Grants:
Panel History:  
Summary on Grant Application Form
We wish to probe the ability of iminium salts to catalyse the epoxidation of alkenes with the aim of producing even greater levels of enantioselectivity than that already obtained. Terpene based iminium salts provide an architecturally rigid framework which should impose significant restrictions on the approach of an alkene to the corresponding iminium salt. Limiting the number of different approaches of the alkene to oxaziridinium salt should enhance the enantioselectivity. It may be possible to prepare the iminium salts in situ from reactions of secondary amines with 1,2-dicarbonyl compounds and this will obviously simplify the procedure. It may also give higher levels of turnover as hydrolysis of the iminium salt will return the amine and 1,2-dicarbonyl compound which can simply react again and reform the iminium salt. It may also be possible to activate imines by metal complexation and we will therefore explore salen metal complexes and oxazoline metal complexes for asymmetric epoxidation.
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Organisation Website: http://www.shef.ac.uk