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Synlett 2001; 2001(8): 1320-1322
DOI: 10.1055/s-2001-16070
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A New Route for the Synthesis of Mono-fluorinated Allyl Alcohols Using the Stereoselective Wittig Olefination via Reaction of (α-flurovinyl)triphenylphosphonium Triflate

Takeshi Hanamoto* , Kazusa Nishiyama, Hiroki Tateishi, Michio Kondo
  • *Department of Chemistry and Applied Chemistry, Saga University, Honjyo-machi 1, Saga 840-8502, Japan; Fax + 81-952-28-87 04; E-mail: hanamoto@cc.saga-u.ac.jp
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Publication Date:
31 December 2001 (online)

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The three-component coupling reaction of (α-fluorovinyl)triphenylphosphonium triflate, cesium allylate, and aldehydes in trimethyl orthoformate gave the corresponding mono-fluorinated allyl ethers with good stereoselectivity; the resulting ethers were readily transformed into the corresponding mono-fluorinated allyl alcohols using the Cp2Zr-mediated reaction.

stereoselective Wittig olefination - mono-fluorinated allyl alcohol - cesium fluoride (CsF) - (α-fluorovinyl)triphenylphosphonium triflate

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