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Application of metallacycles for the synthesis of small molecules




Williams, Catherine Marie, author
Rovis, Tomislav, advisor
Wood, John L., committee member
Finke, Richard G., committee member
Shores, Matthew P., committee member
McNeil, Michael R., committee member

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A method for the nickel-catalyzed hydrocarboxylation of styrene derivatives has been developed that affords exclusively the branched carboxylic acids in moderate to excellent yields. The reaction scope is tolerant of a variety of electron-deficient ortho-, meta-, and para-styrene analogues containing ester, ketone, nitrile, and halide functionalities. The reaction is remarkably efficient, proceeding well with as little as 1 mol% Ni(acac)2 and 2 mol% Cs2CO3. A system for carbon dioxide sequestration and release in organic polymers has been investigated. Although evidence supporting successful carbon dioxide fixation has been found, the envisioned system is not a practical means of sequestration and release. A rapid approach for the synthesis of Abyssomicin C has been developed utilizing the desymmetrization of meso-dimethylglutaric anhydride. Closely modeled after Sorensen's synthesis, our route bypasses the more inefficient beginning steps to intercept the completed synthesis at the Diels-Alder precursor.


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anhydride desymmetrization


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