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Synlett 1997; 1997(6): 716-718
DOI: 10.1055/s-1997-3261
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Highly Stereoselective Synthesis of cis-2-Substituted-3-vinyltetrahydrofurans from (Z)-Trimethyl(5-trimethylsiloxy-2-pentenyl)silane and Acetals

Tomohumi Sano, Takeshi Oriyama*
  • *Department of Chemistry, Faculty of Sciences, Ibaraki University, Bunkyo, Mito 310, Japan
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Publication Date:
31 December 2000 (online)

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A variety of cis-2-substituted-3-vinyltetrahydrofurans are easily and stereoselectively produced by the reaction of acetals with (Z)-trimethyl(5-trimethylsiloxy-2-pentenyl)silane under the influence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate under very mild conditions.

acetal - (Z)-trimethyl(5-trimethylsiloxy-2-pentenyl)silane - cis-2-substituted-3-vinyltetrahydrofuran - trimethylsilyl triflate - stereoselective