Catalytic asymmetric synthesis of Non-proteinogenic amino acids PhD
- Entry requirements:
- 3 years
- not available
- Reference number:
- Start date:
- 01 July 2018
- UK/EU fees:
- International fees:
- Application deadline:
- 01 April 2018
in the UK for Chemistry
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Chiral amino acids whether proteinogenic (derived from proteins) or non-proteinogenic are ubiquitous and integral building blocks of numerous natural products and drug candidate molecules (e.g. antibiotics vancomycin / amoxicillin). Currently the bench mark synthetic methodology for installing this chiral centre is the asymmetric Strecker reaction, which relies on using highly toxic HCN or TMSCN as its key reagent.
This research programme will address this issue by the formation of this key chiral centre contained within non-proteinogenic aryl- and hetero-aryl glycine amino acids via an asymmetric addition of arenes / heteroarenes to allenamides: a reaction commonly known as ‘hydroarylation’. Allenamides have become an increasingly valuable group of compounds that contain two double-bonds on an adjacent carbon which are then attached directly to a nitrogen atom tempered with an electron withdrawing functionality. We have previously shown that it is possible to selectively activate allenamides to nucleophilic attack using ‘gold-catalysis’. We will introduce this new chiral centre by an asymmetric ‘gold-catalysed’ hydroarylation reaction manifold. Once this ‘gold catalysed asymmetric hydroarylation’ transformation has been achieved the products of this transformation will then be converted, in only one synthetic step, to the desired aryl- and hetero-aryl glycine targets.
See: Kimber et al., Org. Lett. 2014, 16, 4606; Tet. Lett, 2015, 56, 350; Synlett 2012, 565; J. Org. Chem. 2010, 75, 5406; Org. Lett. 2010, 12, 1128.
Primary supervisor: Dr Marc Kimber
Applicants should have, or expect to achieve, at least a 2:1 Honours degree (or equivalent) in Chemistry/Medicinal Chemistry.
A relevant Master's degree and / or experience in one or more of the following will be an advantage:
Chemistry / Medicinal Chemistry.
All students must also meet the minimum English Language requirements.
Fees and funding
Tuition fees cover the cost of your teaching, assessment and operating University facilities such as the library, IT equipment and other support services. University fees and charges can be paid in advance and there are several methods of payment, including online payments and payment by instalment. Special arrangements are made for payments by part-time students.
This is an open call for candidates who are sponsored or who have their own funding. If you do not have funding, you may still apply, however Institutional funding is not guaranteed. Outstanding candidates (UK/EU/International) without funding will be considered for funding opportunities which may become available in the School.
How to apply
All applications should be made online. Under programme name, select Chemistry. Please quote reference number: CM/MCK-2/2017