Catalytic Enantioselective Strain Release For The Synthesis Of Chiral Cycloalkanes

Lead Research Organisation: University of Oxford
Department Name: Oxford Chemistry


Demand for food production is projected to increase by 70% in 2050 due to increasing global population. As such, food security is of vital significance worldwide. In this regard, pyrethroid insecticides, which usually feature gem-dimethyl cyclopropane core, play an important role in reducing the yield losses caused by pests and increase the productivity of agriculture.
During this Fellowship, we propose to exploit our modular and tunable superbase catalyst platform, to design, discover and develop new iminophosphorane catalyst systems that will allow the enantioselective synthesis of chiral alkylidenecyclopropanes (ACPs), thus achieving the efficient synthesis of a library of chiral cyclopropanes. Given that cyclopropanes' prevalence in natural products and pharmaceutical molecules like marketed antiplatelet drug Ticagrelor and antiviral cyclopropavir, this strategy can be further applied in the enantioselective synthesis of pyrothroid insecticides and biologically relevant products. In a similar vein, this strategy would be applicable in the construction of enantioenriched cyclobutanes, which are also common motifs in bioactive molecules and versatile intermediates in organic synthesis. This proposal includes both the transfer of knowledge to the host institution and the training of the candidate in new advanced techniques. Results have the potential capacity to be applied in industrial production (i.e. Bayer).


10 25 50