PHOSCOM · Synthetic routes to useful phosphorus compounds

Final Activity Report Summary - PHOSCOM (Synthetic Routes to Useful Phosphorus Compounds)

This project was a collabpration between the university of York (UK) and Celtic Catalysts (Ireland). It was designed to leverage the synergies between UoY's expertise in spartein chemistry with Celtic Catalysts' expertise in development of chemical catalytic routes to chiral compounds. Specifically, with regard to UoY the objectives were: To invent & develop novel industrially relevant organolithium/sparteine processes; To scale these processes for preparation of high value materials; To integrate industry awareness & project management skills. For Celtic Catalysts, the objectives were: To learn and integrate ability to make catalysts using organolithium/sparteine chemistry; Make new molecules to help develop key chemical platform; Make specific high value compounds for sale; All of these project objectives were successfully met. In particular the following successes are noteworthy: Development of very strong links between the partners which have blossomed into another collaboration beyond this project. Created links with new University (IT). Increased profile of the Company in academic circles. Has led to new collaborations and relationships with Universities. Better perception with Customers. Involvement in different area of chemistry has added credibility. Increased Sales New useful products to sell (catalysts & intermediates). With regard to the evolution and scientific results of the project: The project commenced with a comprehensive study of the stoichiometric asymmetric lithiation-trapping of a series of novel phosphine boranes, sulphides and oxides. This was done using different reaction conditions and allowed for optimal conditions to be identified. The methodology developed in this part of the project was then applied to the synthesis of novel bis-phosphine ligands which were then tested by the company for utility in industrially relevant reactions. The methodology developed in this period was then successfully applied to the synthesis of a commercial sample of a ligand fo which Celtic Catalysts had received a customer enquiry. In this instance the expertise developed in this project proved crucial in being able to meet this customer need. This also served as excellent validation of the commercial nature of the project as a whole and helped to "iron out" minor difficulties encountered in relation to the scale-up of these compounds. This phase then led to further scientific developments namely the discovery (which was unexpected) of properties related to the configurationally instability of lithiated phosphine boranes, sulphides and oxides. This in turn led to a one-ligand catalytic asymmetric synthesis of compounds of this type and the methodology was applied to the synthesis of various ligands with potential industrial utility. It should also be noted that in parallel with the above work, some investigations into kinetic resolutions were undertaken but this was to limited success.

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