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Asymmetric ‘Clip-Cycle’ Reactions: A General Enantioselective Synthesis of Cyclic Amines

  • Full or part time
    Dr P Clarke
  • Application Deadline
    Wednesday, January 09, 2019
  • Competition Funded PhD Project (European/UK Students Only)
    Competition Funded PhD Project (European/UK Students Only)

Project Description

Cyclic amines are privileged pharmacophores present in many drug molecules and biologically active natural products, with the 5- and 6-membered rings by far and away the most prevalent. Significantly, cyclic amines occur in 59% of FDA approved drug molecules. Within this subset, piperidines are the most abundant, followed by piperazines in 3rd place, and pyrrolidines in 5th place. The -lactam unit, which is derived from cyclic amines ties with piperazines for 3rd place.1 Natural products such as alkaloids are also loaded with these structural units, which are key to their biological activity. As the chemical synthesis of new compounds is the limiting factor in drug discovery, new methods to synthesise efficiently these privileged ring systems, with control over regio-, diastereo- and enantioselectivity is of paramount importance. The group has developed a highly enantioselective synthesis of functionalised chiral pyrrolidines, via an aza-Michael aminocyclisation reaction, and we now wish to extend this strategy to the synthesis of the 1st and 3rd most abundant pharmacophores in drug molecules. To this end, the proposal aims to: (i) develop an operationally simple, scalable and general catalytic asymmetric method for the synthesis of substituted piperidines, pyrrolidines and piperazines as single enantiomers, from either acyclic achiral or racemic starting materials; and, (ii) apply it to the synthesis of pharmaceutical and natural products containing these heterocyclic units.

All research students follow our innovative Doctoral Training in Chemistry (iDTC): cohort-based training to support the development of scientific, transferable and employability skills. All research students take the core training package which provides both a grounding in the skills required for their research, and transferable skills to enhance employability opportunities following graduation. Core training is progressive and takes place at appropriate points throughout a student’s higher degree programme, with the majority of training taking place in Year 1. In conjunction with the Core training, students, in consultation with their supervisor(s), select training related to the area of their research.
The Clarke group trains all members in contemporary synthetic organic chemistry techniques including the handling of air sensitive reagents, toxic chemicals, and reaction safety analysis and structure determination by advanced spectroscopic methods. This project will also require the student to be trained in HPLC and GC techniques for the monitoring of reactions and determination of product enantioselectivies. The student will attend weekly group meetings focusing on the development of literature awareness, presentation of results, problem solving and mechanistic skills. Guidance will also be given on project management and project specific scientific issues. As part of the Organic Chemistry section the student will be exposed to a wide range of visiting speakers through a vibrant external seminar program. The student will also be encouraged to present their work as a poster and as oral presentations at least two different national or international meetings.

The Department of Chemistry holds an Athena SWAN Gold Award and is committed to supporting equality and diversity for all staff and students. The Department strives to provide a working environment which allows all staff and students to contribute fully, to flourish, and to excel: https://www.york.ac.uk/chemistry/ed/. This PhD project is available to study full-time or part-time (50%).

This PhD will formally start on 1 October 2019. Induction activities will start on 30 September.

1. E. Vitaku, D. T. Smith, J. T. Njardarson, J. Med. Chem. 2014, 57, 10257.

Funding Notes

Fully funded for 3 years by either the Engineering and Physical Sciences Research Council or a Chemistry Teaching Studentship and cover: (i) a tax-free annual stipend at the standard Research Council rate (£14,777 for 2018-19), (ii) tuition fees at the UK/EU rate, (iii) funding for consumables. You do not need to apply separately for the EPSRC funding. However you need to submit a separate Teaching Studentship application: View Website
Teaching studentships are available to any student who is eligible to pay tuition fees at the home rate. ESPRC Studentships are available to any student who meets the EPSRC eligibility criteria: View Website

References

• Applicants should submit an application for a PhD in Chemistry by 9 January 2019
• Supervisors may contact their preferred candidates either by email, telephone, web-chat or in person
• Supervisors may nominate up to two candidates to the assessment panel
• The assessment panel will shortlist candidates for interview from all those nominated
• Shortlisted candidates will be invited to a panel interview at the University of York on 13 or 15 February 2019
• The Awards Panel will award studentships following the panel interviews
• Candidates will be notified of the outcome of the panel’s decision by email

How good is research at University of York in Chemistry?

FTE Category A staff submitted: 47.06

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

Click here to see the results for all UK universities

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