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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 

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