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Synlett 1991; 1991(5): 317-318
DOI: 10.1055/s-1991-34728
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New Sequential Carbon-Carbon Bond Forming Reactions. A Samarium(II) Iodide Mediated Vinylogous Barbier Reaction Followed by an Aldol Reaction

Dennis P. Curran* , Ronald L. Wolin
  • *Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA
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Publication Date:
07 March 2002 (online)

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Reduction of 4-(3-iodopropyl)cyclopent-2-en-1-ones 1 and 7 with 2.5 equivalents of samarium(II) iodide in tetrahydrofuran containing 10 equivalents of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) produces bicyclic samarium enolates that can be protonated to give simple bicyclo[3.3.0]octan-3-ones, or reacted with aldehydes to give functionalized bicyclo[3.3.0]octan-3-ones. Depending on the structure of the aldehyde, a rapid intramolecular Tishchenko reaction may follow the aldol reaction.