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Sodium as a workhorse metal for the atom efficient enantioselective synthesis of bioactive heterocycles

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  • Full or part time
    Prof Steven Bull
  • Application Deadline
    No more applications being accepted
  • Competition Funded PhD Project (Students Worldwide)
    Competition Funded PhD Project (Students Worldwide)

Project Description

The Centre for Sustainable Chemical Technologies (CSCT) at the University of Bath has launched a joint PhD programme with Monash University, Australia.

This project is one of a number that are in competition for up to four funded studentships. More details are available here: http://www.csct.ac.uk/study-with-us/

Home institution: Monash University

Supervisor at Monash: Prof. Phil Andrews (lead) and Dr Vicki Blair
Supervisor at Bath: Prof Steven Bull

Context

While the first organometallic compounds were comprised of Na, synthetic implementation of organosodium reagents has idled when compared to Li equivalents. Application has been hampered by hazardous preparative methods,1, 2 as well as generally inferior atom economy. However, there are considerable environmental advantages that Na metal boasts over its counterparts.3-5 In particular, it is easily obtainable from ocean water given its abundance is approximately nine times greater than Mg and more than 3 x 104 that of Li, making it effectively an infinite resource on which organometallic chemists can rely upon. Recent promising developments have shown convenient preparation of strong bases, such as Na diisopropylamide, can be obtained directly from Na metal using electron carriers, such as isoprene.6, 7 This method is completely halogen free and effectively reduces the number of metal atoms required per equivalent of base, by half. Furthermore, an altered form of this method has proven effective in preparation of sodium (S)-N-(α-methylbenzyl)propylenamide- a precursor that can be used in a highly efficient diastereoselective cascade reaction.8 This procedure yields six new contiguous chiral centers from two consecutive Michael additions followed by a ring annulation step, with this highly stereoselctive methodology having been used to generate a diverse library of novel chiral cyclohexylamine derivatives.

Recent expansion of this work has shown this type of reactive Na enolate intermediate to be highly versatile that can be used for the convenient preparation of highly functionalised aldehydes with a high degree of stereocontrol. Of particular interest is the potential to trap the intermediate with imines to allow for a three component, one-pot synthesis of a series of novel antibacterial β-lactam rings that can be further functionalised via their synthetically versatile aldehyde functional groups.

β-Lactams are critical component of families of antibiotics such as cephalosporins, carbapenems and carbacephems that are key for treating many chronic bacterial infections. Unfortunately, many of these β-lactams have developed drug resistance in bacteria emanating from the evolution of bacterial metallo-lactamases. Therefore, new designer β-lactam drugs are needed which are not affected by this enzyme and so this new synthetic approach has the potential to provide a vital new weapon in the armoury of antimicrobials available for clinicians.

Application process

We invite applications from Science and Engineering graduates who have, or expect to obtain, a first or upper second class degree and have a strong interest in Sustainable & Circular Technologies.

You MUST express interest for three projects in order of preference – you can see all projects here: https://www.csct.ac.uk/bath-monash-global-phd-programme/ . Please submit your application at the Home institution of your preferred project (‘Home’ institution details can be found in the project summary). However, please note that you are applying for a joint PhD programme and applications will be processed as such.

Monash University

Expressions of interest (EoI) can be lodged through https://www.monash.edu/science/bath-monash-program. The EoI should provide the following information:
CV including details of citizenship, your Official Academic Transcripts, key to grades/grading scale of your transcripts, evidence of English language proficiency (IELTS or TOEFL, for full requirements see: https://www.monash.edu/graduate-research/faqs-and-resources/content/chapter-two/2-2), and two referees and contact details (optional). You must provide a link to these documents in Section 8 using Google Drive (Instructions in Section 8).

University of Bath

Please submit your application through the following link: https://www.csct.ac.uk/bath-monash-global-phd-programme/
Please make sure to mention in the “finance” section of your application that you are applying for funding through the joint Bath/Monash PhD programme for your specified projects.

In the “research interests” section of your application, please name the three projects you are interested in and rank them in order of preference. Please also include the names of the Bath lead supervisors.

Funding Notes

Bath Monash PhD studentships include tuition fee sponsorship and a living allowance (stipend) for the course duration (up to 42 months maximum). Note, however, that studentships for Bath-based projects will provide cover for UK/EU tuition fees ONLY. Non-Australian nationals studying in Australia will be required to pay their own Overseas Student Health Cover (OSHC).

Additional and suitably qualified applicants who can access a scholarship/studentship from other sources will be also considered.

References

1. M. Schlosser, Angewandte Chemie International Edition in English, 1964, 3, 362-373.
2. M. Schlosser, Angewandte Chemie International Edition in English, 1964, 3, 287-306.
3. T. C. Wanger, Conservation Letters, 2011, 4, 202-206.
4. V. Flexer, C. F. Baspineiro and C. I. Galli, Sci. Total Environ., 2018, 639, 1188-1204.
5. C. Grosjean, P. H. Miranda, M. Perrin and P. Poggi, Renewable and Sustainable Energy Reviews, 2012, 16, 1735-1744.
6. P. C. Andrews, N. D. R. Barnett, R. E. Mulvey, W. Clegg, P. A. O'Neil, D. Barr, L. Cowton, A. J. Dawson and B. J. Wakefield, J. Organomet. Chem., 1996, 518, 85-95.
7. D. Barr, A. J. Dawson and B. J. Wakefield, J. Chem. Soc., Chem. Commun., 1992, 204-204.
8. M. Koutsaplis, P. C. Andrews, S. D. Bull, P. J. Duggan, B. H. Fraser and P. Jensen, Chem. Commun., 2007, 3580-3582.

How good is research at University of Bath in Chemistry?

FTE Category A staff submitted: 33.10

Research output data provided by the Research Excellence Framework (REF)

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