The Triple Way: Combining Pot, Atom and Step Economy (PASE) for Greener Organic Synthesis

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This project is aimed the development of a procedure for a one pot, atom and step economic synthesis of highly substituted THPs and piperidines. Atom economy, is the concept of every atom of each reagent being used is included in the desired product of the reaction. Step economy is the drive to reduce the number of synthetic steps (and hence the associated waste such as solvents used in the reaction, solvents used in work-up and product isolation, solvents used in product purification, silica gel or related substances used in chromatographic purification, contaminated aqueous waste generated from cleaning equipment and glassware, etc ) in the synthesis of any given target molecule. One pot reactions take the concept of step economy to its ultimate conclusion. That is the ability to complete an entire multi-step, multi-reaction synthesis in a single pot. If this can be achieved the problems of waste highlighted above would have been obviated. Application of these concepts embody Principles 1, 2, 5 and 8 of the Twelve Principles of Green Chemistry, and should ultimately lead to the `ideal synthesis', which is a one step, one pot, atom economic construction of a target molecule from cheap, renewable starting materials in a 100% yield.In this project we propose to combine our expertise in the synthesis of organic molecules with the general expertise in Green Chemistry in the School of Chemistry at the University of Nottingham. This project is aimed at combining atom and step economy for the first time for the synthesis of small and medium sized molecules. Firstly, we will apply this strategy to the synthesis of tetrahydropyrans (THP). Secondly, we will apply this strategy to the synthesis of piperidines. These molecules are of considerable importance to the pharmaceutical, agrochemical and biotech industries.This work is both adventurous and speculative making it appropriate for EPSRC funding. However, if successful it will lead to shorter, cleaner and greener synthetic routes to these important classes of molecules. We seek CRYSTAL/EPRRC funding for manpower and consumables to carry out a two year proof of principle study