A study of the reactivity of (methyl 2-acetamidoacrylate)-tricarbonyliron(0) leading to a novel synthesis of β,β,β-trialkyl α-amino acids |
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Authors: | James Barker Stephen L CookM Elena Lasterra-Snchez Susan E Thomas |
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Institution: | James Barker,Stephen L. CookM. Elena Lasterra-Sánchez,Susan E. Thomas |
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Abstract: | (Methyl 2-acetamidoacrylate)tricarbonyliron(0) (3) reacts with 2 equivalents of methyllithium to give methyl N-acetylalaninate (4) and 2-acetamido-4-oxopentanoate (5) when the reaction is quenched with trifluoroacetic acid. Production of methyl N-acetylalaninate is dependent only on the presence of trifluoroacetic acid, and the ratio of 4 to 5 generated in these reactions is related to the quantity of trifluoroacetic acid used to quench them. Addition of two equivalents of methyllithium followed by tertiary haloalkanes gives protected β,β,β-trialkyl α-amino acids which may be hydrolysed to give tert-leucine (13) and the new α-amino acids 2-amino-3,3-dimethylpentanoic acid (14) and 2-amino-3,3-dimethylhexanoic acid (15). |
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Keywords: | Iron complexes Carbonyl complexes Amino acid complexes |
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