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Highlights in Chemical Science

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Enzyme-like catalyst for organic reactions


22 February 2006


Amino acid derivatives found in numerous potent bioactive substances can be made in a single step, report researchers in the UK.

Darren Dixon and colleagues at the University of Manchester have prepared a simple organic catalyst for the Mannich reaction. The reaction is a key route to forming carbon-carbon bonds and allows enantioselective synthesis of various beta-amino acid motifs that are present in many biologically active natural products and pharmaceutical compounds.

 

                    Enzyme-like catalyst

 

Dixon's catalyst functions like an enzyme and aids the reaction in two ways. A bridgehead nitrogen activates the nucleophile while a bulky thiourea group uses hydrogen bonding to simultaneously organise the electrophile. The 3D arrangement of catalyst and reagents ensures that the reaction occurs with high levels of stereocontrol. 

The group is now looking at using this catalyst in other key enantioselective organic reactions. 'The number of potential electrophiles and pro-nucleophiles is vast and therefore a large number of new, highly selective asymmetric reactions are waiting to be discovered,' said Dixon.
 
Nina Athey-Pollard

References

A L Tillman, J Ye and D J Dixon, Chem. Comm., 2006 (DOI: 10.1039/b515725k)