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oai:figshare.com:article/32994977 2026-05-01T00:00:00Z portal_693 item_type_8 month_year_05_2026

Synthesis, Vinylation and Rearrangement of NH-Isoxazolines and Copper Catalyzed 6 Pi Electrocyclization Dylan Cole Keane (24399965) Methodology Enaminones are a privileged motif that have both nucleophilic and electrophilic reactivity embedded within. Finding new ways to access these compounds is of high interest. The Anderson group is interested in utilizing [3,3] sigmatropic rearrangements to access new N-heterocycles in diastereoselective fashion. The work described in Chapter 1 features a new method for accessing enaminones utilizing a cascade approach that features an N–vinylisoxazoline intermediate that undergoes [3,3] sigmatropic rearrangement to form densely functionalized exocyclic vinylogous pyrrolidines. The functionalization of these compounds showcased a unique reactivity at the gem-dione under basic conditions and the mechanism of the corresponding products was further investigated. Chapter 2 discusses a ring expansion reaction of azetidine–N–oxides to form highly functionalized isoxazolidine products with up to 3 contiguous stereocenters in excellent diastereoselectivity. The scope was explored and shown to be tolerant for a wide array of aniline nucleophiles as well as a limited number of amines and alcohols with various azetidine–N–oxides. Chapter 3 is centered around establishing a method for copper catalyzed 6 π electrocyclization to form morpholines and morpholine–N–oxides via an initial Chan–Lam coupling followed by spontaneous electrocyclization. 2026-05-01T00:00:00Z Text Thesis 10.25417/uic.32994977.v1 https://figshare.com/articles/thesis/Synthesis_Vinylation_and_Rearrangement_of_NH-Isoxazolines_and_Copper_Catalyzed_6_Pi_Electrocyclization/32994977 In Copyright Open Access after 2028-05-01