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Details of Grant 

EPSRC Reference: GR/M87283/01
Title: CONFORMATIONAL INTERLOCKING AND REMOTE STEREOCONTROL
Principal Investigator: Clayden, Professor J
Other Investigators:
Researcher Co-Investigators:
Project Partners:
Department: Chemistry
Organisation: Victoria University of Manchester, The
Scheme: Standard Research (Pre-FEC)
Starts: 07 November 2000 Ends: 06 November 2003 Value (£): 173,929
EPSRC Research Topic Classifications:
Chemical Synthetic Methodology
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors Chemicals
Pharmaceuticals and Biotechnology
Related Grants:
Panel History:  
Summary on Grant Application Form
We aim to apply what we know of the conformation of some simple aromatic amides to the synthetic challenge of remote stereocontrol. We will then set out to learn more about the way that the conformation of other more versatile functional groups controls the stereoselectivity of nearby reactions. In this way, we aim to develop a general way of transferring stereochemistry from one site in a molecule to another by exploiting the conformational interactions that exist among the intervening functional groups. The first stages will use tertiary amides to mediate the formation of new stereogenic centres up to 12 atoms away from a controlling centre. We will move onto make this controlling centre part of a removable chiral auxiliary, allowing action at a distance control over absolute stereochemistry. Amides are hard to remove at a later stage, and a key part of the project will involve (a) finding out how to control the conformation of other functional groups (sulfones, carbamates, ethers, and esters) and (b) how to use their conformation to control stereoselective nucleophilic and electrophilic attack at prochiral centres. Finally we aim to demonstrate the conceptual advances we hope to make in some syntheses of biologically and structurally important molecules.
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