Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of α-Ketobutyrolactones and γ-Hydroxy-α-Keto Acids

  • Kang, Han-Young (Department of Chemistry and Institute for Basic Sciences, Chungbuk National University) ;
  • Ji, Yu-Mi (Department of Chemistry and Institute for Basic Sciences, Chungbuk National University) ;
  • Yu, Yeon-Kwon (Department of Chemistry and Institute for Basic Sciences, Chungbuk National University) ;
  • Yu, Ji-Yeon (Department of Chemistry and Institute for Basic Sciences, Chungbuk National University) ;
  • Lee, Young-Hoon (Department of Chemistry and Center for Molecular Design and Synthesis, Korea Advanced Institute of Science and Technology) ;
  • Lee, Sang-Joon (Department of Chemistry and Center for Molecular Design and Synthesis, Korea Advanced Institute of Science and Technology)
  • Published : 2003.12.20
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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 ${\gamma}$-hydroxy-${\alpha}$-keto acids has been successfully achieved. For racemic form of ${\gamma}$-hydroxy-${\alpha}$-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 ${\alpha}$-ketobutyrolactones. Enzymatic resolution of the ${\gamma}$-hydroxy-${\alpha}$-methylene esters provided the desired${\gamma}$-hydroxy-${\alpha}$-methylene acids which were successfully converted to ${\gamma}$-hydroxy-${\alpha}$-ketobutyrolactones in optically pure forms.

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References

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