Asymmetric "Clip-Cycle" Reactions: Cyclic amines and ethers are important structural units present in many pharmaceutical agents and natural products. The ability to synthesise these units with control of both relative and absolute stereochemistry is becoming increasingly important. In this project we are developing the asymmetric oxa- and aza-Michael reactions of substituted unsaturated thioesters for the synthesis of pyrrolidines, piperidines, THFs and THPs from both achiral and chiral racemic precursors. These methods will be applied to the synthesis of both polyketide and alkaloid containing natural products.

 

 

 

 

 

 

 

 

 

 

 

 

 

PASE synthesis: We have developed a pot, atom and step economic (PASE) synthesis of highly substituted tetrahydropyranones and piperidines, based on the Maitland-Japp reaction. Our work has delivered enantioselective versions of this reaction, which generate THPs in 99%e.e. We are now focused on expanding the utility of this reaction to enable the asymmetric synthesis of piperidine rings and structurally diverse 3D-heterocyclic fragments which are of substantial interest to medicinal chemists for the development of new drug molecules.

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