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  • The Synthesis of Spirocycles via C–H Insertion

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    Lombard_2016_01Thesis.pdf (9.137Mb)
    Author(s)
    Lombard, Fanny Julie Amandine
    Primary Supervisor
    Coster, Mark
    Other Supervisors
    Poulsen, Sally-Ann
    Year published
    2016
    Metadata
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    Abstract
    This thesis describes the design and development of a new methodology for the synthesis of spiroacetals involving a rhodium(II)-catalysed C–H insertion of suitable diazo precur- sors. Three generations of diazo precursors were designed, synthesised and treated with Rh(II) catalysts: The 1st generation precursor consisted of a phenyl substituted tetrahydropyranyl acetal bearing a proximal phenyl diazoketone substituent, which underwent Rh(II)-catalysed C– H insertion to give unexpected spirocyclic orthoesters. DFT calculations showed that these ’anomalous’ products are formed by a mechanism involving hydride transfer to the ...
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    This thesis describes the design and development of a new methodology for the synthesis of spiroacetals involving a rhodium(II)-catalysed C–H insertion of suitable diazo precur- sors. Three generations of diazo precursors were designed, synthesised and treated with Rh(II) catalysts: The 1st generation precursor consisted of a phenyl substituted tetrahydropyranyl acetal bearing a proximal phenyl diazoketone substituent, which underwent Rh(II)-catalysed C– H insertion to give unexpected spirocyclic orthoesters. DFT calculations showed that these ’anomalous’ products are formed by a mechanism involving hydride transfer to the rhodium carbene followed by intramolecular C–O bond formation.
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    Thesis Type
    Thesis (PhD Doctorate)
    Degree Program
    Doctor of Philosophy (PhD)
    School
    School of Natural Sciences
    DOI
    https://doi.org/10.25904/1912/3549
    Copyright Statement
    The author owns the copyright in this thesis, unless stated otherwise.
    Item Access Status
    Public
    Subject
    Spiroacetals
    C–H insertion
    Phenyl substituted tetrahydropyranyl
    Rhodium(II)-catalysed C–H insertion
    Publication URI
    http://hdl.handle.net/10072/367715
    Collection
    • Theses - Higher Degree by Research

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