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Synlett 1996; 1996(9): 850-852
DOI: 10.1055/s-1996-5591
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2-Methyl-1,3-Cyclopentane and -Cyclohexanediones: Nucleophiles and Leaving Groups in Palladium-Catalyzed Allylations

Nicolas Vicart, Jacques Goré, Bernard Cazes*
  • *Université Claude Bernard, Laboratoire de Chimie Organique I, CNRS UMR 5622, CPE-Lyon, 43 Bd. du 11 Novembre 1918, 69622 Villeurbanne, France, Fax: 33 + 72.43.12.14, E-mail: cazes@univ-lyon1.fr
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Publication Date:
31 December 2000 (online)

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2-Allyl-2-methyl-1,3-cyclopentanediones and -cyclohexanediones 5 have been demonstrated to be isomerized under thermodynamic control or to be substituted by a malonate anion in the presence of a palladium catalyst. This nucleophile exchange, following a first palladium-mediated substitution of acrolein dimethyl acetal, gives a new access to methoxyallyl malonate 9.

1,3-cyclalkanedione - π-allyl palladium - acrolein dimethyl acetal - isomerization - thermodynamic control - nucleophile exchange