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Catalytic asymmetric synthesis of epoxides and aziridines using sulfur ylides


Research objectives and content
The host laboratory have 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 this project we wish to seek alternative and less potentially hazardous methods for generating metallocarbenes and now propose to use zinc carbenoids. Such species can be easily prepared from dialkyl zinc and diiodomethane. We will study conditions under which the zinc carbenoids can be generated and attempt to carry out epoxidations using catalytic amounts og sulfides. Then we will prepare chiral sulfides and apply this to asymmetric epoxidation. 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 lahoratory have strong links with industry and Zeneca and Sheffield University will be patenting this work if it is successful.

Funding Scheme

RGI - Research grants (individual fellowships)


Brook Hill
S3 7HF Sheffield
United Kingdom

Participants (1)

Not available