The Triple Way: Combining Pot, Atom and Step Economy (PASE) for Greener Organic Synthesis
Lead Research Organisation:
University of York
Department Name: Chemistry
Abstract
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
Organisations
People |
ORCID iD |
Paul Clarke (Principal Investigator) |
Publications
Clarke P
(2007)
Combining pot, atom and step economy (PASE) in organic synthesis. Synthesis of tetrahydropyran-4-ones
in Green Chemistry
Clarke P
(2007)
Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation
in Tetrahedron Letters
Clarke P
(2008)
Pot, Atom, and Step Economic (PASE) Synthesis of Highly Substituted Piperidines: A Five-Component Condensation
in Synthesis
Clarke PA
(2008)
One-pot synthesis of functionalized piperid-4-ones: a four-component condensation.
in Organic letters
Liu Z
(2009)
Corrosion performance and restoration of laser-formed metallic alloy sheets
in Journal of Laser Applications
Description | The Pot, Atom and Step Economic synthesis of piperidines was developed. Also developed was an asymmetric pot, atom and step economic synthesi sof highly functionalised tetrahydropyrans |
Exploitation Route | GSK is now funding a follow-on project to further develope these methods for the synthesis drug-like 3D-fragments. Out key findings and paper have been used to define the concept of pot, atom and step economy and has been cited over 75 times |
Sectors | Chemicals,Pharmaceuticals and Medical Biotechnology |
Description | A Pot, Atom and Step Economic synthesis of highly functionalised piperidines was developed. |
Sector | Chemicals,Pharmaceuticals and Medical Biotechnology |