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Filtering by: Committee Member Humprey, Philip E. Remove constraint Committee Member: Humprey, Philip E. Advisor Blakemore, Paul R. Remove constraint Advisor: Blakemore, Paul R.

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  • Broadening the scope of the modified-Julia reaction : a mild and stereoselective method for the synthesis of (Z)-configurated α,β-unsaturated lactones

    Creator:
    Giesbrecht, Heath Eugene
    Abstract:
    An intramolecular variant of the modified-Julia olefination was demonstrated by the synthesis of α,β-unsaturated lactones in a mild and (Z)-selective fashion. The lynchpin reagent (benzothiazol-2-sulfonyl) acetic acid was synthesized in a straightforward fashion in 86% overall yield from commercially available 2-mercaptobenzothiazole via conversion to ethyl (benzothiazol-2-ylthio)acetate by base mediated alkylation...
    Resource Type:
    Masters Thesis
    Full Text:
    the coupling reaction………………………….. 6 2. E-selectivity exhibited for unsaturated (aromatic

  • Development of Methods for Stereoselective Carbon-Carbon Bond Formation

    Creator:
    Wu, Zhenhua
    Abstract:
    Three distinct methods to achieve the stereoselective synthesis of carbon-carbon bonds were investigated, encompassing: (i) the formation of axially chiral biaryl molecules by enantioselective Suzuki cross-coupling, (ii) the synthesis of α-phenylalkylboronic esters by enantioselective chain extension, and (iii) the stereospecific synthesis of alkenes by eliminative cross-coupling of enantioenriched sp³-hybridized carbenoids....
    Resource Type:
    Dissertation
    Full Text:
    the targeted alkene [(E)- or (Z)- isomer] as determined by choice of carbenoid stereochemical pairing