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Synlett 1995; 1995(10): 1004-1006
DOI: 10.1055/s-1995-5190
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Highly Regioselective Tin-Mediated Ring-Opening of 2,3-Epoxy Alcohol Derivatives With Trimethylsilyl Halide

Takeshi Oriyama* , Akihiro Ishiwata, Yoko Hori, Tetsuo Yatabe, Naomi Hasumi, Gen Koga
  • *Department of Chemistry, Faculty of Science, Ibaraki University, Bunkyo, Mito 310, Japan
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Publication Date:
31 December 2000 (online)

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The oxirane ring of 2,3-epoxy alcohol derivatives are shown to be cleaved regioselectively at C3-O to give O-acetylated vicinal halohydrins when reacted with trimethylsilyl halide in the presence of tin(II) halide as a catalyst followed by treatment with acetyl halide.

ring-opening - 2,3-epoxy alcohol - regioselective tin(II) halide - trimethylsilyl halide