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The Synthesis And Reactivity Of Novel Donor-Acceptor Cyclopropanes And Progress Towards Pyrrolidine Alkaloids, Michael R. Emmett

Electronic Thesis and Dissertation Repository

The first chapter of this thesis focuses on the synthesis and reactivity of cyclopropane hemimalonates. The cyclopropane hemimalonates can easily be synthesized from 1,1-cyclopropanediesters. The reactivity of cyclopropane hemimalonates with indole under ultra-high pressure conditions leads to ring opened adducts that are complementary to previous research in the Kerr group. The tandem ring opening decarboxylation reaction of cyclopropane hemimalonates led to the synthesis of γ-aminobutyric acid analogues. When an external nucleophile was not present, the cyclopropane hemimalonates could rearrange to form butyrolactones in good to excellent yields. The stereochemical integrity of the cyclopropane hemimalonate is retained through this process, which …