Synthesis of hydroxy acids using asymmetric hydrogenation in water.

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Authors
Dunn, Zachary.
Issue Date
2013-09-17
Type
Thesis
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en_US
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Undergraduate research. , Undergraduate thesis.
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Abstract
The purpose of this study was to develop a green chemistry synthesis of hydroxy acids from the starting material glyoxylic acid. Two reactions that were the primary focus of this study. The first was the Wittig-Horner reaction that converted methyl 2-(diethylphosphoryl)-2-(O-benzoyl) ethanoate into the enol esters methyl 2-(O-benzoyl)-3-(p-methoxyphenyl) propenoate and methyl 2-(O-benzoyl)-4-methyl pentenoate. It was shown that these reactions proceeded at -10°C, compared to previously described methods at -78°C. The second focus was the asymmetric hydrogenation of the enol ester to create a protected hydroxy acid. The hydrogenation was attempted using conditions normally known to create protected amino acids; 50°C, 24 hour reaction time, and water as the only solvent. However, the asymmetric hydrogenation of both methyl 2-(O-benzoyl)-3-(p-methoxyphenyl) propenoate and methyl 2-(O-benzoyl)-4-methyl pentenoate yielded no product.
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59 leaves : illustrations.
Thesis--Departmental honors in Biochemistry.
Bibliography: leaves 48-50.
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Wheaton College (Norton, Mass.)
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