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Synlett 1997; 1997(7): 845-847
DOI: 10.1055/s-1997-5755
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Sequential Michael Addition-Carbocyclization Reactions: A Palladium-Mediated Approach to Highly Functionalized 3-Methylenetetrahydrofurans

Xavier Marat, Nuno Monteiro, Geneviève Balme*
  • *Laboratoire de chimie organique I, associé au CNRS, Université Claude Bernard, CPE, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France, Fax: (0)4.72.43.12.14, E-mail: balme@univ-lyon1.fr
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Publication Date:
31 December 2000 (online)

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A one-pot procedure for the preparation of highly functionalized 3-methylenetetrahydrofurans is described. The methodology is based on an oxygen nucleophile initiated Michael addition of propargyl alcohols to alkylidene or arylidenemalonates followed in situ by a palladium-mediated exo-dig cyclization.

oxygen initiated Michael addition - palladium mediated exo-dig carbocyclization - 3-methylenetetrahydrofuran synthesis