Catalytic and asymmetric carbonyl epoxidation

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Project objective

Research objectives and content The host group has previously discovered a novel catalytic cycle for epoxidation of carbonyl compounds using just catalytic quantities of sulfides, metal salts, and diazocompounds (this work was patented by Zeneca). In order to make this process less hazardous, the in situ generation of the diazocompounds has been considered and indeed found to be successful. However, none of the simple chiral sulfides based on oxathianes have worked in the catalytic process and so new classes of chiral sulfides need to be prepared to render this practical, catalytic cycle asymmetric. Once we have found simple chiral sulfides that are effective, we will scale up the process and demonstrate its applicability to the preparation of a broad range of epoxides. In essence, the process constitutes the coupling of two aldehydes to give epoxides with control over relative and absolute stereochemistry and that is atom economical and powerful. This process will also be applied to asymmetric aziridination. Training content (objective, benefit and expected impact) The chemistry involves the use and handling of sensitive reagents and therefore provides excellent training in careful experimentation. Furthermore, the work will require the use of the all of the most up-to-date analytical techniques and so will provide comprehensive training. The chemistry described could become one of the best methods for the direct preparation of epoxides and this will have a major impact both in academia and industry. Links with industry / industrial relevance (22) The host laboratory has strong links with industry (they currently collaborate with 8 different chemical companies) and Sheffield University will be patenting this work if it is successful. Epoxides are intermediates in an increasing number of potential drugs so are critical to the pharmaceutical industry.

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Participants

• UNIVERSITY OF SHEFFIELD · SHEFFIELDCoordinatorUnited Kingdom

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