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Organocatalytic vinylogous reactions
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Fraboni, Americo Jeffrey. Organocatalytic vinylogous reactions. Retrieved from https://doi.org/doi:10.7282/T3K64MDS

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TitleOrganocatalytic vinylogous reactions
NameFraboni, Americo Jeffrey (author); Brenner-Moyer, Stacey E. (chair); Huskey, Phil (internal member); Szostak, Michal (internal member); Hyster, Todd (outside member); Rutgers University; Graduate School - Newark
Date Created2016
Other Date2016-10 (degree)
SubjectChemistry
Extent1 online resource (xxviii, 242 p. : ill.)
DescriptionWhile organocatalysis has emerged as a significant component in modern organic synthesis, being recognized as the third pillar of catalysis, alongside biocatalysis and transition metal catalysis, its scope is still relatively limited. This is particularly the case with dienamine catalysis, in which the majority of reactions developed have been DielsAlder-type cylcoadditions or have been focused on functionalization in the α-position, due to issues with stereoselectivity and regioselectivity in the remote γ-position. As such, the development of linear asymmetric γ-functionalizations and organocascades has great potential to introduce novel complexity to α,β-unsaturated aldehydes and provide precursors to biologically relevant molecules. This dissertation presents a comprehensive review of dienamine catalysis, as well as the development of novel linear organocatalytic vinylogous functionalizations of α,β-unsaturated aldehydes. With the goal of generating diversity through cascades and heteroatomic substrates, the research conducted was focused on four main topics: 1). The synthesis of γ-amino alcohols via a novel dienamine-iminium cascade involving a γ-amination, followed by transfer hydrogenation. 2). Exploration into the potential of this cascade to provide heteroatomic asymmetric complexity with the introduction of different nucleophiles, and the many difficulties that arise from these reactions. 3). The development of an unprecedented metal-free allylic oxidation, forming various nitrones via a novel dienamine catalyzed redox mechanism, which displayed unique divergent reactivity that could be exploited to obtain varied libraries of heterocyclic compounds. 4). The synthesis of analogues to elucidate the absolute stereochemistry of an organocatalytic vinylogous Michael product. These studies have illustrated the potential, as well as some of the limitations of dienamine catalysis.
NotePh.D.
NoteIncludes bibliographical references
Noteby Americo Jeffrey Fraboni
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3K64MDS
Languageeng
CollectionGraduate School - Newark Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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