New Methods for Stereoselective 1,3-Difunctionalization of Cyclopropanes

With the support of the Chemical Synthesis Program in the Division of Chemistry, Professor Qiu Wang of Duke University is studying new ways to use cyclopropanes as building blocks in organic synthesis. Catalytic methods are being developed that transform readily available cyclopropanes that lack traditional activating structural features, into high-value richly functionalized products that can be used in many industries, such as agriculture, consumer household products, materials, and those related to human health. These activities are providing training opportunities for students in organic synthesis and catalytic new method development. Outreach efforts are also being pursued to improve the STEM training pipeline, broaden student participation in research, and engage the local community. Synthetic applications of simple cyclopropanes to deliver versatile functionalized products without specific activating groups are highly attractive yet represent unmet challenges for organic chemists. Professor Wang and her research team are developing new catalysts and novel methods to achieve selective ring-opening/1,3-difunctionalization reactions of non-activated cyclopropanes. Strategies in copper catalysis, photocatalysis, and electrochemistry are being investigated to promote regio- and enantioselective carbon-carbon bond cleavage of cyclopropanes for the synthesis of 1,3-difunctionalized compounds and heterocyclic frameworks. New fundamental insights obtained in these studies are being used to further develop new multi-component processes for the preparation of highly sought-after targets in organic synthesis, medicinal chemistry, and agrochemicals. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.