About the Project
Research in the O’Hagan Group has had a major focus on the synthesis of novel organofluorine motifs, and in particular placing fluorines stereoselectively around aliphatic ring systems. This is synthetically challenging and has opened up a new area of organic chemistry. In 2015 we prepared a landmark molecule, all-syn 1,2,3,4,5,6-hexafluorocyclohexane,[1] which emerged as the most polar aliphatic compound prepared to date. It has the interesting property of have an electronegative fluorine face and an electropositive hydrogen face. The molecule will bind anions and cations,[2] which is very unusual for an aliphatic ring. We wish to carry on work with this and related motifs eg all-syn 1,2,3-trifluorocyclopropane. This project will involve organic synthesis and with a particular specialism in fluorine. It will be interdisciplinary and explore incorporating these polar ring systems into biologically active molecules[3] to explore for example how the rings interact with the amino acid residues of proteins and enzymes.
References
[1] N. S. Keddie, A. M. Z. Slawin, T. Lebl, D. Philp, D. O’Hagan, All-cis 1,2,3,4,5,6-hexafluorocyclohexane is a facially polarised cyclohexane motif.’ Nature Chem.,2015, 7, 483.
[2] B. E. Ziegler, M. Lecours, R. A. Marta, J. Featherstone, E. Fillion, W. S. Hopkins, V. Steinmetz, N. S. Keddie, D. O’Hagan, T. B. McMahon, ‘Janus face aspect of all-cis 1,2,3,4,5,6-hexafluorocyclohexane dictates remarkable anion and cation interactions in the gas phase.’ J. Am. Chem. Soc., 2016, 138, 7460
[3] T. Bykova, N. Al-Maharik, A. M. Z. Slawin, M. Bühl, T. Lebl, D. O’ Hagan, ‘Benzylic functionalisation of phenyl all cis-2, 3, 5, 6 -tetrafluoro -cyclohexane provides access to new organo-fluorine building blocks.’, Chem. Eur. J., 2018, 24, 13290 - 13296.
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