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    Synthesis and Decarboxylative Coupling of Sulfonyl Acetic Esters

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    Weaver_ku_0099D_10924_DATA_1.pdf (9.587Mb)
    Issue Date
    2010-04-28
    Author
    Weaver, Jimmie D.
    Publisher
    University of Kansas
    Format
    322 pages
    Type
    Dissertation
    Degree Level
    Ph.D.
    Discipline
    Chemistry
    Rights
    This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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    Abstract
    The synthesis and palladium-catalyzed decarboxylative allylation (DCA) of α-sulfonyl allyl esters is the central focus of this dissertation. Specifically we describe the development of the racemic reaction in which the scope and mechanism are investigated. In addition, we demonstrate the superiority of Pd-catalyzed DCA to current methodology for the formation of tertiary sulfones. Furthermore, we demonstrate how the chemistry of the sulfone and the DCA, we developed, can be used in concert to obtain products that are not easily accessible. We next developed an asymmetric variant of the reaction in which the asymmetry comes from the substrate itself and not an outside source. Specifically, we observed high levels of conservation of enantioenrichment when the reaction proceeded in the presence of an achiral or racemic catalyst. We investigated this unusual behavior and propose a mechanism to explain the observation. Again, we compare the DCA to existing methodologies and demonstrate that it compares very favorably synthetically and in part answers unsolved challenges in asymmetric organic chemistry. In the course of this work it became apparent that the synthesis of our starting materials would also be a significant contribution to the field of organic chemistry. We have detailed the syntheses of both asymmetric and racemic sulfonyl acetic esters.
    URI
    http://hdl.handle.net/1808/6473
    Collections
    • Dissertations [4472]
    • Chemistry Dissertations and Theses [336]

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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