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Synthesis 1994; 1994(6): 592-596
DOI: 10.1055/s-1994-25529
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Enantiocomplementary Resolution of 2-Phenylthio-2-cyclopentenol and 2-Phenylthio-2-cyclohexenol Using the Same Lipase

Seiichi Takano* , Osamu Yamada, Hirokazu Lida, Kunio Ogasawara
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan
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Publication Date:
17 September 2002 (online)

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Both racemic 2-phenylthio-2-cyclopentenol (±)-(3a) and 2-phenylthio-2-cyclohexenol (±)-(3b) afford the corresponding (R)-acetates (R)-4a,b and the unreacted (S)-alcohols (S)-3a,b, respectively, in excellent optical and chemical yields on treatment with vinyl acetate in the presence of lipase PS in dichloromethane. On the other hand, both racemic acetates (±)-4a,b obtained from racemic 2-phenylthio-2-cyclopentenol (±)-(3a) and 2-phenylthio-2-cyclohexenol (±)-(3b) afford the corresponding (R)-alcohols (R)-3a,b and the unreacted (S)-acetates (S)-4a,b, respectively, in excellent optical and chemical yields on stirring in a phosphate buffer-acetone solution in the presence of the same lipase.