Copper-promoted and catalyzed alkene difunctionalization reactions: Diamination, aminooxygenation and oxyamination
Sequeira, Fatima Clementina
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Nitrogen heterocycles are ubiquitous in biologically active molecules. The development of new chemical methods which provide an efficient and concise synthesis of these molecules is a prevalent topic. The research described herein strives to expand and demonstrate the utility of copper(II)-difunctionalization reactions of alkenes for the formation of nitrogen heterocycles. In Chapter 1, a new copper(II)-promoted intra/intermolecular olefin diamination is discussed, in which an intramolecular nitrogen inserted onto the unactivated alkene, followed by the addition of an external nitrogen nucleophile. This reaction allows a wide range of unsaturated amines to form various five-membered nitrogen heterocycles, with pendent methylene amino substitution. Chapter 2 focused on the expansion of the copper(II) difunctionalization reaction to include larger ring systems of six-membered nitrogen heterocycles, such as morpholine, through a new Cu(II)-oxyamination reaction. Finally, in Chapter 3, we demonstrated the efficiency of a Cu(II)-catalyzed enantioselective intramolecular aminooxygenation of alkenes by expanding the reaction on a multi-gram scale without reducing the efficiency and enantioselectivity of the reaction. This method provides a viable synthetic route to chiral indolines, which are prevalent in medicinal chemistry research.