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Synthesis 1987; 1987(4): 389-390
DOI: 10.1055/s-1987-27956
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Synthesis of Enantiomerically Pure (4S)-2-Alken-4-olides via (2S)-1-Phenylsulfonyl-2-alkanols

Rikuhei Tanikaga* , Ken Hosoya, Aritsune Kaji
  • *Department of Chemistry, Faculty of Science, Kyoto University, Sakyo-ku, Kyoto 606, Japan
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Publication Date:
20 August 2002 (online)

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Reduction of 1-chloro-3-phenylsulfonyl-2-propanone with baker's yeast, followed by epoxidation and alkylation with Grignard reagents, yields enantiomerically pure (2S)-2-phenylsulfonyl-2-alkanols, which are converted into (4S)-2-alken-4-olides in 100% e. e.