Copper-Catalyzed Synthesis of Saturated Oxygen and Nitrogen Heterocycles by Alkene Difunctionalization
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The complexity of the molecules are usually the factors contributing to their observed biological and physiological properties. Synthetic organic chemistry has been a tool used by achieving such complexity by starting from simple molecules, synthons. Difunctionalization of alkenes is one of the most commonly used techniques to achieve various heterocycles such as pyrrolidines or cyclic ethers. Those heterocycles are oftentimes found in many biologically active molecules found in nature or synthetic origin. The research presented herein aimed to investigate novel methodologies to achieve such transformation using the copper complex as the catalyst. In chapter I, a novel copper-catalyzed coupling reaction between olefins and potassium β-aminoethyl trifluoroborates – Routes to Diversely functionalized pyrrolidines is reported. The method allows access to a wide range of pyrrolidines motifs by starting from readily available or easily accessible olefins and potassium β-aminoethyl trifluoroborates. Chapter II describes the coupling of alkyltrifluoroborates with unsaturated alkenols and unsaturated carboxylic acids. Promising asymmetric catalysis results were also achieved in this study. Chapter III details the copper-catalyzed enantioselective synthesis of spirocyclic ethers. This work is a joint effort between Dr. Shuklendu Karyakarte, Ilyas Berhane and myself. This method can be used to synthesize enantioenriched spirocyclic ethers by starting from 1,1-disubstituted alkenols. The [5,5]- and [5,6]- fused spirocyclic ethers were successfully synthesized with good yield and high ee.