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Filtering by: Committee Member O'Neill, J. Philip Remove constraint Committee Member: O'Neill, J. Philip Advisor Blakemore, Paul R. Remove constraint Advisor: Blakemore, Paul R. Rights Statement In Copyright Remove constraint Rights Statement: In Copyright

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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:
    …………………………… 39 32. 12-membered α,β-unsaturated lactone formation………... 40 33. 13-membered α,β-unsaturated

  • 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:
    boronates with a combination of O- (-lithiobenzyl)-N,N-diisopropylcarbamate and ligand 3,3-bis[(4S)-4,5

  • Total synthesis of sparteine alkaloids from a common tetraoxobispidine intermediate

    Creator:
    Melbardis, John
    Abstract:
    In previous work (Blakemore et al. Org. Lett. 2005, 7, 4721; Heterocycles 2006, 70, 609), successful elaborations of the lupine alkaloids (±)-α-isosparteine (dl-2) and (±)-β-isosparteine (dl-3) were realized from a common tetraoxobispidine precursor, 3,7-diallyl -2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (93). Herein, the tetraoxobispidine approach to lupine alkaloids was extended to a total synthesis of...
    Resource Type:
    Masters Thesis
    Full Text:
    ). N NH N NH N NH2 35 39 40 HRef. 43 Schopf (1962) NH2OCH3 MeOH-H2O, rt 98% H OCH3 O O