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Synthesis 1993; 1993(5): 513-516
DOI: 10.1055/s-1993-25895
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Practical Synthesis of Optically Pure Methyl (2R,3S)-2,3-Epoxybutanoate via Microbial Asymmetric Reduction of α-Chloroacetoacetate

Hiroyuki Akita* , Reiko Todoroki, Hiroshi Endo, Yoshinobu Ikari, Takeshi Oishi
  • *School of Pharmaceutical Science, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274, Japan
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Publication Date:
17 September 2002 (online)

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Asymmetric reduction of ethyl α-chloroacetoacetate (3) with Baker's yeast followed by treatment with sodium ethoxide afforded a mixture of ethyl (2R,3S)-( 8) and (2S,3S)-2,3-epoxybutanoate (9) (8/9, 85:15), which could be converted into the optically pure methyl (2R,3S)-2,3-epoxybutanoate (25) via one recrystallization of the brucine salt of the diastereomeric mixture of the corresponding epoxy acid.