Opioids as enantioselective organocatalysts
Long, Shelly (2012) Opioids as enantioselective organocatalysts. PhD thesis, Dublin City University.
Full text available as:
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.
Archive Staff Only: edit this record