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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 24, Number 12
BKCSDE 24(12)
December 20, 2003 

Synthesis of α-Ketobutyrolactones and γ-Hydroxy-α-Keto Acids
Han-Young Kang,* Yumi Ji, Yeon-Kwon Yu, Ji-Yeon Yu, Younghoon Lee, Sang-Joon Lee
α-Ketobutyrolactones, γ-Hydroxy-α-keto acids, Indium, Enzymes, Enantiomeric resolution
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.
1819 - 1826
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