Commercial interests in fluorine chemistry emerged in the eighties mainly due to the need to replace industrial chlorofluorocarbons but also because of the increasing use of organofluorine compounds in agrochemical, medicinal and in material science.
Rational design exploiting the remarkable properties of F or CF3-containing group or substructures has been successful in the development of new and effective biochemical tools as well as medicinal and therapeutic agents.
Nevertheless, progress is still hampered by the lack of general methodologies to access fluorinated compounds, more particularly homochiral targets or building blocks that feature a trifluoromethylated stereogenic centre.
The development of new strategies to prepare organofluorine compounds remains indeed a challenge employing novel approaches to control the regio-, diastereo- and enantioselectivity of new fluorination or trifluoromethylation processes. The current proposal builds on our emerging interest in the use of organosilanes as starting materials for the preparation of various novel trifluoromethylated targets.
We will study both a catalytic asymmetric Diels-Alder reaction using trifluoromethylated building blocks and explore a tandem cycloaddition/trifluoromethylation route with the aim to prepare structurally diverse trifluoromethylated carbo- and heterocycles.
With these compounds in hand, we hope to improve our understanding of H/CF3 substitution effects by studying their physicochemical properties. Properties to be measured are solubility, lipophilicity/polarity, membrane permeation, acidity/basicity of surrounding groups and conformation.
This type of study is important for drug discovery. The work will be carried out in the Chemistry Research Laboratory at the University of Ox ford by Arnaud Tessier under the supervision of Dr V. Gouverneur.
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