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Exploring the New Chemistry of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes

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Title: Exploring the New Chemistry of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes
Author: Tait, Katrina Marie
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
Abstract: Synthetic organic chemistry is at the center of drug design/development, which uses literature reactions to create biologically active compounds. A downfall to this approach is that there is still so much unknown about the reactivity profile of organic bicyclic molecules. While many heterobicyclic alkenes have been studied, there are significantly fewer reports about the reactivity of 3-aza-2-oxabicyclo[2.2.1]hept-5-enes. The first part of this work examines the Lewis acid-catalyzed ring-opening/rearrangement of 3-aza-2-oxabicyclo[2.2.1]hept-5-enes to form a cyclized nitrone or oxazolidinone product depending on the catalyst. The next section investigates the ruthenium-catalyzed ring-opening and isomerization of 3-aza-2-oxabicylo[2.2.1]hept-5-enes in the presence of amines. Ruthenium mediates the ring-opening to form an unsaturated aminocyclopentenol product which undergoes allylic alcohol isomerization to provide the corresponding cyclopentanone. The final section first investigates the cyclopropanation of 3-aza-2-oxabicyclo[2.2.1]hept-5-enes under palladium catalysis with diazomethane which was well tolerated for various substrates. The latter part of this section focuses on the acid-catalyzed nucleophilic ring-opening reaction of the previously synthesized cyclopropanated substrate with alcohols. The substrate undergoes ring-opening through C-O bond cleavage to form a substituted methanocyclopentane product.
Date: 2018-01-11

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