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Filtering by: Creator Jackson, Alexis M. Remove constraint Creator: Jackson, Alexis M. Advisor Blakemore, Paul R. Remove constraint Advisor: Blakemore, Paul R. Degree Field Chemistry Remove constraint Degree Field: Chemistry

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  • Investigation of Chain Extension Approaches for the Stereoselective Reagent-Controlled Synthesis of alpha-Heteroatom Substituted Alkyl Boronic Esters

    Creator:
    Barsamian, Adam L.
    Abstract:
    Two distinct strategies were explored for the enantioselective synthesis of α-heteroatom substituted alkyl boronic esters by stereoselective reagent-controlled homologation using transient chiral carbenoid reagents CHYMX (Y = heteroatom, X = nucleofuge, M = electrofuge). In the first case, a stereospecific reagent-controlled homologation (sStReCH) approach to α-alkoxyalkylboronates using α-metalated S,O- and...
    Resource Type:
    Dissertation
    Full Text:
    transient chiral carbenoid reagents CHYMX (Y = heteroatom, X = nucleofuge, M = electrofuge). In the first

  • Stereospecific Synthesis of Stereotriad Motifs and Alkenes Using Enantioenriched sp³-Hybridized Carbenoids

    Creator:
    Xun, Sun
    Abstract:
    Enantioenriched sp³-hybridized carbenoid reagents CR1R2MX (X = nucleofuge, M = electrofuge) of different types were investigated for the synthesis of polysubstituted alkyl chains by iterative stereospecific reagent-controlled homologation (StReCH) and for the stereospecific connective synthesis of alkenes by eliminative cross-coupling. In the first part, putative enantioenriched α-chloroalkyllithiums (CHRLiCl) were employed...
    Resource Type:
    Dissertation
    Full Text:
    = nucleofuge, M = electrofuge) of different types were investigated for the synthesis of polysubstituted

  • Analysis of the mechanism of sulfoxide-lithium exchange and the reactive intermediate in stereospecific reagent-controlled homologation (StReCH)

    Creator:
    Hoyt, Amanda
    Abstract:
    The stereospecific reagent-controlled homologation (StReCH) of boronic esters with enantioenriched carbenoid species generated in situ by the addition of organolithium initiators to stereodefined α-chloroalkyl aryl sulfoxides was previously reported. The reaction of an organolithium with an α-chloroalkyl aryl sulfoxide ostensibly generates an α-chloroalkyllithium via sulfoxide-lithium exchange; however, the true nature...
    Resource Type:
    Masters Thesis
    Full Text:
    Preparative chromatographic separations were performed on silica gel 60 (35-75 μm) and reactions followed by

  • Synthesis and catalytic applications of derivatives of 7,7'-dihydroxy-8,8'-biquinolyl (azaBINOL)

    Creator:
    Wang, Chao
    Abstract:
    The synthesis of axially chiral polyfunctional derivatives of 8,8'-biquinolyl was explored and the catalytic action of appropriate derivative types investigated in three separate processes: (1) the silylcyanation of carbonyl groups and imines, (2) alkylation of a glycine Schiff-base via phase transfer-catalysis, and (3) direct amide bond formation from simple amines...
    Resource Type:
    Dissertation
    Full Text:
    performance in the silylcyanation of benzaldehyde, as noted in the text. Mr. Darrin M. Flanigan conducted

  • Stereocontrolled Synthesis of Allenes by Eliminative Cross-Coupling of Carbenoids

    Creator:
    Cao, Yang
    Abstract:
    The bimolecular reaction of two carbenoid species resulting in the formation of a carbon-carbon double bond (pi-system), referred to herein as carbenoid eliminative cross-coupling (CEXC), involves a series of three fundamental steps: (i) ate-complex formation (transmetalation), (ii) 1,2-metalate rearrangement, and (iii) beta-elimination. All three steps are stereospecific and so the...
    Resource Type:
    Dissertation
    Full Text:
    stereocenter of carbenoid (55) remains the same, the another stereocenter of R2 R1 M’ X’ R3 R4M X M