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Non-covalent catalysis breakthrough

Courtesy Department of Chemistry Photography

Dr Robert Phipps and his group have used chiral non-covalent catalysis to enable a well-known chemical reaction that is used in pharmaceutical drug discovery to be carried out in a new way.

Synthetic chemists tend to be most familiar with using covalent bonds to coordinate the assembly of molecules, but the Phipps group has been concentrating on harnessing the potential of non-covalent interactions – where two atoms still interact with each other, but don’t permanently share a pair of electrons as they do in covalent bonding.

In a paper published in Science last week, Dr Phipps and two PhD students, Rupert Proctor and Holly Davis, describe how they have used chiral non-covalent catalysis to append new groups to basic heteroarenes, such as pyridine and quinoline, in an enantioselective manner, which has not been done before.  

This reaction is valuable because similar compounds are commonly used in the search for new drug therapies and alternative methods to access these compounds in enantioenriched form typically require numerous reaction steps. In their paper, Catalytic Enantioselective Minisci-Type Addition to Heteroarenesthe Phipps Group are able to obtain their targets in a rapid fashion and with very high levels of stereocontrol. 

 “We are really excited by these results as they demonstrate how powerful non-covalent catalysis can be for controlling enantioselectivity in the context of what is seen as a very challenging reaction," said Dr Phipps. "We are currently working to gain more information on the mechanism and are exploring a number of different directions with this chemistry.”