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EPSRC Reference:
EP/E012272/1
Title:
Determining the Barrier to Inversion of Chiral Organometallics
Principal Investigator:
Coldham, Professor I
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department:
Chemistry
Organisation:
University of Sheffield
Scheme:
Standard Research
Starts:
01 July 2007
Ends:
30 June 2010
Value (£):
131,634
EPSRC Research Topic Classifications:
Asymmetric Chemistry
Physical Organic Chemistry
EPSRC Industrial Sector Classifications:
Chemicals
Related Grants:
Panel History:
Panel Date
Panel Name
Outcome
02 Jun 2006
Physical Organic Chemistry Sift Panel (Science)
Deferred
Summary on Grant Application Form
The research outlined in this proposal is in the area of physical organic chemistry. In particular, it involves the study of organometallic species. We have determined the barrier to inversion of 2-lithiopyrrolidines and applied this knowledge to their highly enantioselective dynamic resolution, leading to the asymmetric preparation of 2-substituted pyrrolidines. The aim of this research is to build on this expertise and apply it to other organometallic species. We plan to use a combination of NMR spectroscopy and conventional electrophilic quench/chiral chromatographic analysis to determine the rate of interconversion of the mirror images of selected chiral organometallic species.This will allow comparison of different substituted derivatives and will therefore provide valuable information on the influence of these substituents on the enantiomerization process. This will include all different types of organometallic species, from non-stabilized to dipole stabilized (especially organometallics alpha to oxygen and nitrogen) to mesomerically stabilized (benzyl and allyl species).With quantitative rate data to hand for these enantiomerizations, we will study the effect of ligands on this process, including chiral ligands. This knowledge will then be used to explore dynamic resolution of the organometallics and the mechanism for this resolution.
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Project URL:
Further Information:
Organisation Website:
http://www.shef.ac.uk