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Opioids as enantioselective organocatalysts

Long, Shelly (2012) Opioids as enantioselective organocatalysts. PhD thesis, Dublin City University.

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Abstract

The field of organocatalysis has rapidly expanded over the past decade. Advantages of organocatalysts over many metal-based catalysts include air and moisture stability, low cost and potential reduced environmental impact. Moreover, there is no possibility of leaching of metallic species into the product, an important concern in pharmaceutical synthesis. Successful organocatalysts from the chiral pool include examples based on proline and the cinchona alkaloids. These alkaloids are cheap, readily available and contain several functional groups that act as ‘handles’ for further modification. This project investigates the opiates as a hitherto unexplored class of alkaloid organocatalysts. Numerous opioid derivatives are known from the drug design and development process and provide a convenient starting point to expedite the synthesis of ‘hit’ organocatalyst analogues. The functional groups present also offer potential for further structural modification. A series of opioid derivatives have been synthesised, characterised and their potential to act as enantioselective organocatalysts has been evaluated. X-ray crystal structure analysis has been carried out on a number of opioid derivatives. Although enantioselectivities have been modest, our studies prove that the morphinan ‘skeleton’ can be used as a novel chiral scaffold for organocatalysis.

Item Type:Thesis (PhD)
Date of Award:November 2012
Refereed:No
Supervisor(s):Gathergood, Nicholas
Uncontrolled Keywords:Medicinal Chemistry; Catalysis; Organocatalysis
Subjects:Physical Sciences > Organic chemistry
Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Research Initiatives and Centres > National Institute for Cellular Biotechnology (NICB)
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 3.0 License. View License
Funders:Irish Research Council for Science Engineering and Technology, Dublin City University
ID Code:17468
Deposited On:26 Nov 2012 15:59 by Nick Gathergood. Last Modified 26 Nov 2012 15:59

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