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Synlett 1993; 1993(1): 88-90
DOI: 10.1055/s-1993-22360
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Cyclizations of γ-Hydroxyallenes Mediated by Organopalladium Halides: A Convergent Synthetic Route to Substituted 5-Alkenyl-2-furanones and 2-Alkenyltetrahydrofurans

Robert D. Walkup* , Lufeng Guan, Michael D. Mosher, Sang Woong Kim, Young Soo Kim
  • *Department of Chemistry & Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA
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Publication Date:
19 March 2002 (online)

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When a γ-hydroxyallene (various β-allenylcarbinols or 4,5-hexadienoic acid) is allowed to react with aryl or alkenyl halides in the presence of (Ph3P)4Pd and base, cyclization and coupling to form the title compounds in 14 - 78 (average 50)% yields occurs. A mechanism in which an aryl- or alkenylpalladium(II) halide initiates the cyclization by intramolecular oxypalladation is discussed.