Synthesis of α-ketobutyrolactones and γ-hydroxy-α-keto acids

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In connection with the studies for developing new enzymes that could be useful in organic synthesis, practical preparation of racemic and enantiopure forms of γ-hydroxy-α-keto acids has been successfully achieved. For racemic form of γ-hydroxy-α-keto acids, indium-mediated allylation of aldehydes with 2-(bromomethyl)acrylic acid has been employed as a key step. Oxidative cleavage of the thus formed 2-methylenebutyrolactones provided the desired α-ketobutyrolactones. Enzymatic resolution of the γ-hydroxy-α-methylene esters provided the desired γ-hydroxy-α-methylene acids which were successfully converted to γ-hydroxy-α-ketobutyrolactones in optically pure forms.
Publisher
The Korean Chemical Society
Issue Date
2003
Keywords

α-Ketobutyrolactones; γ-Hydroxy-α-keto acids; Indium; Enzymes; Enantiomeric resolution

Citation

bulletin of the korean chemical society, Vol.24, No.12, pp.1819-1826

URI
http://hdl.handle.net/10203/16238
Link
http://journal.kcsnet.or.kr/
Appears in Collection
CH-Journal Papers(저널논문)
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2003.3. Synthesis of α-Ketobutyrolactones and γ-Hydroxy-α-Keto Acids.pdf(264.35 kB)Download

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