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Synlett 2000; 2000(12): 1819-1821
DOI: 10.1055/s-2000-8701
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A New Allylidene Phosphorane Reagent for the Efficient Conversion of Aldehydes to γ,δ-Unsaturated Allyl-β-Ketoesters

Daniel Chapdelaine* , Pascal Dubé, Pierre Deslongchamps
  • *Laboratoire de snythèse organique, Département de chimie, Institut de pharmacologie de Sherbrooke, Université de Sherbrooke, 3001, 13e avenue nord, Sherbrooke, Québec, Canada J1H 5N4; Fax (819)820-6823; E-mail: pierre.deslongchamps@courrier.usherb.ca
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Publication Date:
31 December 2000 (online)

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A new Wittig reagent 4 has been synthesized and its reaction with various aldehydes afforded the corresponding dienol ethers in fair to good yields. Subsequent acid-catalyzed hydrolysis provided γ,δ-unsaturated allyl-β-ketoesters 1.

allylidene phosphorane reagent - dienol ether - γ,δ-unsaturated allyl-β-ketoester - Wittig olefination - hydrolysis