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Details of Grant 

EPSRC Reference: GR/L58064/01
Title: CONVERTING THE STOICHIOMETRIC SULFUR YLIDE REACTION INTO A CATALYTIC PROCESS
Principal Investigator: Aggarwal, Professor VK
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Zeneca
Department: Chemistry
Organisation: University of Sheffield
Scheme: Standard Research (Pre-FEC)
Starts: 01 November 1997 Ends: 28 February 2001 Value (£): 141,735
EPSRC Research Topic Classifications:
Catalysis & Applied Catalysis
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors
Related Grants:
Panel History:  
Summary on Grant Application Form
Epoxides can be prepared from carbonyl compounds using sulfur ylides but the process suffers in requiring stoichiometric amounts of sulfides. We are proposing to convert this reaction into a catalytic process and in particular to develop a process for the preparation of terminal epoxides. Towards this endeavour we have recently discovered a novel catalytic cycle for epoxidation of carbonyl compounds using a sulfide and a combination of Et2Zn/CH2ICl (Simmons Smith). To make the process catalytic in sulfide we have found that use of chelating ligands for zinc allows sub-stoichiometric amounts of sulfides to be used. Furthermore, we have found that such ligands also result in rate acceleration. We will test a range of achiral and chiral ligands to improve the turnover of the sulfide. We will then prepare chiral sulfides and develop a method for catalytic asymmetric epoxidation. Finally. we intend to use the concept of molecular robots for asymmetric epoxidation. In this process, both the ylide and the carbonyl compound are activated towards reaction on a metal template. This should result in higher reactivity, improved rates and selectivity.
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Organisation Website: http://www.shef.ac.uk