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Synlett 1995; 1995(2): 151-152
DOI: 10.1055/s-1995-4895
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A Convenient Synthesis of 5-Substituted-2,3-Dihydrothiophenes

Ian A. O’Neil* , Kathryn M. Hamilton, J. Allen Miller, Robert J. Young
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, U.K.
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Publication Date:
31 December 2000 (online)

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Treatment of γ-thiobutyrolactone with KHMDS and N-(5-chloro-2-pyridyl)triflimide (Comin’s reagent) gives the corresponding thiolenoltriflate in good yields. Coupling of the thiolenoltriflate with Gilman cuprates proceeds smoothly to give the 5-substituted-2,3-dihydrothiophenes. The synthesis of a homochiral thiolactone is described. Conversion to the corresponding thiolenoltriflate proceeds in good yield using the conditions described above. The coupling with Gilman cuprates gives homochiral 5-substituted-2,3-dihydrothiophenes in good yield.

Dihydrothiophenes - Triflate - Cuprate Coupling