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New Strategies for Cyclopropane Synthesis


   Department of Chemistry


About the Project

The cyclopropane moiety is a privileged motif in drug discovery, being the 10th most frequently encountered ring system in small molecule drugs. It is often deployed as an isosteric replacement for an alkene, or as a rigid alkyl linker, and is also used strategically to increase potency, enhance metabolic stability, and reduce off-target effects. New synthetic methods for installation of cyclopropanes remain in high demand. This project will develop new strategies for cyclopropane synthesis using visible light photoredox catalysis in conjunction with flow chemistry.

This is a fully-funded synthetic organic chemistry PhD project in collaboration with the pharmaceutical company AstraZeneca (subject to contractual agreement). It will include a research placement at AZ in Cambridge and close interaction with industrial scientists. It will be ideally suited to anybody with a desire to pursue a synthetic chemistry career in the pharmaceutical industry.

Preferred start date: 1 September 2023. We cannot consider later start dates but an earlier start date may be possible - please contact Dr Alex Cresswell to discuss.

The Cresswell group specialises in the development of new synthetic reactions using visible light photoredox catalysis,[1,2] and all PhD students are exposed to a number of enabling technologies and advanced techniques, including photoredox catalysis, flow chemistry, automation, and mechanistic analysis. Further training will be offered in the form of weekly problem sessions on organic synthesis and participation in compiling an annual review of the literature on synthetic chemistry for drug discovery.

The Department of Chemistry at the University of Bath provides state-of-the-art facilities and a highly supportive environment for our research. The Cresswell group currently comprises 8 PhD students (mostly industry-funded), a PDRA, and a Technical Specialist. We are based in the main Chemistry building in two modern and well-equipped labs. We have two Teledyne-Isco automated chromatography systems and a Teledyne-Isco prep-HPLC system. We also own two Vapourtec continuous flow chemistry platforms (an E-series Easy-Medchem and an R-series RS-400 with full automation, the former equipped with a UV-150 photoreactor), Uniqsis PhotoSyn and Borealis flow photoreactors, and a Huber CC-85 recirculating chiller (for flow photoredox down to –60 °C). Our group has full access to the analytical and technical facilities offered at Bath, including flow NMR spectroscopy for reaction monitoring.

Candidate Requirements:

Applicants should hold, or expect to receive, a First Class or good Upper Second Class Honours degree (or the equivalent) in Chemistry and a strong motivation to carry out technically challenging research in organic synthesis and catalysis. Previous experience of synthetic organic chemistry beyond core undergraduate teaching (e.g. industrial placement) would be beneficial but not essential. A master’s level qualification would also be advantageous.

Non-UK applicants must meet our English language entry requirement.

Enquiries and Applications:

Informal enquiries are welcomed and should be directed to Dr Alex Cresswell ().

Formal applications should be made via the University of Bath’s online application form for a PhD in Chemistry.

More information about applying for a PhD at Bath may be found on our website.

Note - applications may close earlier than the advertised deadline if a suitable candidate is found; therefore, we recommend that you contact Dr Alex Cresswell prior to applying and submit your formal application as early as possible.

Equality, Diversity and Inclusion:

We value a diverse research environment and aim to be an inclusive university, where difference is celebrated and respected. We welcome and encourage applications from under-represented groups.

If you have circumstances that you feel we should be aware of that have affected your educational attainment, then please feel free to tell us about it in your application form. The best way to do this is a short paragraph at the end of your personal statement.


Funding Notes

Candidates applying for this project may be considered for a 4-year EPSRC Industrial CASE studentship with AstraZeneca (subject to contract). Funding covers tuition fees, a stipend (2022/23 UKRI rate £17,668 per annum) and a generous budget for research expenses, training and conference attendance.

References

[1] “Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines” Cresswell et al., J. Am. Chem. Soc. 2021, 143, 15936 [most read JACS article of the month]
[2] “Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines” Cresswell et al., Angew. Chem. Int. Ed. 2020, 59, 14986

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