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    • Graduate School - MU Theses and Dissertations (MU)
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    • 2010 Dissertations (MU)
    • 2010 MU dissertations - Freely available online
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    2,1-Benzothiazines : preparation and reactivity

    Calkins, Nathan L., 1982-
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    Date
    2010
    Format
    Thesis
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    Abstract
    The synthesis of chiral ligands to tune the reactivity and stereoselectivity of many catalytic asymmetric reactions has been given considerable attention in synthetic organic chemistry over the past decade. This report will show the results of efforts toward the syntheses of several families of enantiomerically pure 2,1-benzothiazine ligands. These ligands are unique in that they contain a chiral sulfoximine. Several 2,1-benzothiazine ligands were prepared in single one-pot syntheses and others in as many as five or more steps for larger heterocycles. An optimized synthetic route will be shown for a very well known Buchwald Hartwig N-arylation of sulfoximines and haloarenes. The synthetic procedure for the N-arylation of sulfoximines synthetic procedure has virtually been unchanged since its introduction in 1998. The new synthesis herein has dramatically improved reaction time and scope for the N-arylation of aryl bromides and aryl chlorides. Until now, aryl chloride based N-arylations gave extremely poor conversions when attempted thermally. Lastly, unsubstituted and 4-phenyl substituted 2,1-benzothiazine lithiation reactivity will be discussed for the sulfoximine stabilized lithium vinyl carbanions. Mono- and di-substitutions are now synthetically possible. New synthetic strategies for accessing the ortho-S-phenyl ring as a viable carbanion will also be shown.
    URI
    https://hdl.handle.net/10355/8309
    https://doi.org/10.32469/10355/8309
    Degree
    Ph. D.
    Thesis Department
    Chemistry (MU)
    Rights
    OpenAccess.
    This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License.
    Collections
    • 2010 MU dissertations - Freely available online
    • Chemistry electronic theses and dissertations (MU)

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