The Catalytic Enantioselective Construction of All-Carbon Quaternary Centres

Our research programme spans the broad area of synthetic organic chemistry and focuses on the development of new and efficient synthetic methodologies for the catalytic construction of novel molecular building blocks in an enantioselective manner. We are particularly interested in the development of new palladium-catalysed decarboxylative C–C bond formation processes as a means of generating structurally complex sp3-rich molecules to facilitate the drug discovery efforts in the pharmaceutical industry. The proposed PhD project will focus specifically on the catalytic enantioselective alkenylation of carbonyl compounds as a means of generating highly congested sp3 all-carbon quaternary stereogenic centres in an asymmetric fashion.
It is well established that compounds lacking in structural complexity (sp2-rich) have a poorer track record of being developed into commercial pharmaceuticals than those which possess a more varied 3-D shape (sp3-rich). Towards this end, we have developed the first chemo- and regioselective palladium-catalysed decarboxylative alkenylation of 1,3-dicarbonyls with oxygen (Org. Lett. 2013, 15, 3778), nitrogen (J. Org. Chem., 2016, submitted) and carbon (Org. Lett. 2015, 17, 3926) nucleophiles. This process generates two new bonds and congested quaternary all-carbon centres in a single step. Owing to the efficiency of this approach, this PhD project will explore the use of chiral ligands for palladium to couple 1,3-dicarbonyl compounds with a range of nucleophiles and install these chiral centres in an enantioselective fashion. The development of this methodology will allow us to access extensive classes of novel chiral building blocks as crucial intermediates for drug discovery.
Enantioselective catalysis is a world-leading area of research in organic chemistry and the Department of Chemistry at Lancaster boasts state-of-the-art NMR, mass spectrometry and HPLC facilities to undertake this work. As such, you will be provided with excellent practical skills in synthetic chemistry as well as an in-depth knowledge of organic chemistry. If you are passionate about organic synthesis and are interested in working in our laboratory, do apply via the Lancaster Postgraduate Admissions website or e-mail me if you require further information.

The Chemistry Department operates a research student mentor programme. One of our current student mentors will be available to answer any of your questions about life and studying in our Department throughout the application stage and during your research degree at Lancaster.
The Chemistry Department particularly welcomes applications from women. We are committed to flexible working on an individual basis, we welcome and embrace diversity, and are committed to the Athena SWAN principles.
The Department is the holder of the Athena Swan Bronze Award.