Asymmetric hydrogenation of tyrosine analogues in water.
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"The purpose of this study was to investigate the feasibility of using water for the synthesis of tyrosine analogues through asymmetric hydrogenation reactions. A variety of α-enamide substrates, varying in R groups and location on the benzene ring, were synthesized including methyl-2-(benzoylamino)-3-(p-butoxyphenyl)-propenoate, methyl-2-(benzoylamino)-3-(o-methoxyphenyl)-propenoate, and methyl-2-(benzoylamino)-3-(p-methoxyphenyl)-propenoate. These substrates were subsequently hydrogenated in water at 60 psi to produce methyl-2-(benzoylamino)-3-(p-methoxyphenyl)-propanoate, methyl-2-(benzoylamino)-3-(o-methoxyphenyl)-propanoate, and methyl-2-(benzoylamino)-3-(p-butoxyphenyl)-propanoate. These results confirmed that water can be used as the solvent for asymmetric hydrogenations of enamide ester materials to synthesize tyrosine analogues."
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Amy Moreira 2013 Honors Thesis.pdf