Palladium-Catalyzed Annulation of Monosubstituted β-Diketones

Frédéric Buono; Alphonse Tenaglia

doi:10.1055/s-1998-1865

Synlett 1998; 1998(10): 1153-1155
DOI: 10.1055/s-1998-1865

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Palladium-Catalyzed Annulation of Monosubstituted β-Diketones

Frédéric Buono^* , Alphonse Tenaglia

^*Laboratoire de Synthèse Asymétrique, ENSSPICAM, UMR 6516, Faculté des Sciences de St Jérôme, Av. Escadrille Normandie-Niemen, F-13397 Marseille Cedex 20, France; Fax (+33)4 91 02 77 76; E-mail: tenaglia@spi-chim.u-3mrs.fr

Abstract

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Various 4-methylenecyclohexanones and bridged bicyclo[3.n.1]alkanones (n = 2 or 3) are readily available via a palladium-catalyzed C,C-dialkylative cyclisation of monoalkylated β-diketones with allylic diacetate 1a (or dicarbonate 1b). A one-pot bicycloannulation/retro Claisen fragmentation leading to medium-sized cycloalkanones from monoalkylated cyclic β-diketones is described.

cycloalkanones - β-diketones - C-C bond formation - palladium catalyst - annulation

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