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Synlett 1992; 1992(4): 349-350
DOI: 10.1055/s-1992-22011
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Palladium-Catalyzed Site-Differentiating Coupling of a Chiral Cyclopentenol Derivative with Racemic 3-Hydroxyalkenyl Iodide: New Chemical Resolution of 4-Alkenyl-3-hydroxy-cyclopentanones

Sigeru Torii* , Hiroshi Okumoto, Takayuki Kotani
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Tsushima-naka, Okayama 700, Japan
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Publication Date:
08 March 2002 (online)

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Optically active mono-protected 2-cyclopentene-1,4-diol (+)-1 was site-selectively coupled with (±)-(Z)-3-tert-butyldimethylsiloxy-1-octenyl iodide [(±)-2] in the presence of a palladium catalyst, followed by separation and acid treatment to give (+)- and (-)-3-hydroxy-4-(3-hydroxy-1-octenyl)cyclopentanone [(+)-6 and (-)-6] in pure form.