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Synthesis 1992; 1992(4): 365-366
DOI: 10.1055/s-1992-26110
short paper
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Chemoenzymatic Synthesis of (R)-(-)-Citramalic Acid

Shangjin Yang* , Walter Hayden, Kurt Faber, Herfried Griengl
  • *Christian Doppler Laboratory for the Chemistry of Chiral Compounds at the Institute of Organic Chemistry, Graz University of Technology, Stremayrgasse 16, A-8010 Graz, Austria
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Publication Date:
17 September 2002 (online)

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Dimethyl (R)-(-)-citramalate (dimethyl 2-hydroxy-2-methylsuccinate, 4) was prepared in ≍ 50% overall yield in four steps from ethyl chloro(hydroxyimino)acetate and ethyl methacrylate. The key transformation involved a regio- and enantiospecific hydrolysis of diethyl (RS)-5-methyl-4, 5-dihydroisoxazole-3,5-dicarboxylate (1a) using a protease from Aspergillus oryzae.