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Synlett 1998; 1998(9): 998-1000
DOI: 10.1055/s-1998-1828
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Directed Palladium-Catalyzed Cascade Cyclization as an Approach to trans- and cis-Hexahydro-1H-benz[f]indenes

Isabelle Coudanne* , Geneviève Balme
  • *Laboratoire de chimie organique I, associé au CNRS, Université Claude Bernard, CPE, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France; Fax Int.33.4.72.43.12.14; E-mail: balme@univ.lyon1.fr
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Publication Date:
31 December 2000 (online)

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The hydrogenation of the acetylenic substrate 6 followed by a palladium-catalyzed cascade bis-cyclization process led to a trans-hexahydro-1H-benz[f]indene. By changing the order of the two preceding steps, only the cis-hexahydro-1H-benz[f]indene structure was obtained.

Wacker-type reaction - palladium - trans-hexahydro-1H-benz[f]indene - cis-hexahydro-1H-benz[f]indene