A Dramatic Effect of the Reaction Conditions on the Course of a Palladium-Catalyzed Cyclization of an Alkene Bearing a Vinyl Bromide and a Nucleophile: A New Route to the trans-Hydrindane System

Isabelle Coudanne; Jaume Castro; Geneviève Balme

doi:10.1055/s-1998-1829

Synlett 1998; 1998(9): 995-997
DOI: 10.1055/s-1998-1829

letter

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A Dramatic Effect of the Reaction Conditions on the Course of a Palladium-Catalyzed Cyclization of an Alkene Bearing a Vinyl Bromide and a Nucleophile: A New Route to the trans-Hydrindane System

Isabelle Coudanne^* , Jaume Castro, 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

Abstract

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Upon treatment with catalytic Pd(dppe) in the presence of KH, the malonate derivative 3 underwent a Wacker-type cyclization leading exclusively to compound 4 having the trans-hydrindane system. However, the course of the cyclization is dramatically dependent on the reaction conditions, mainly on the nature of the base. In the presence of a carbonate, a quaternary ammonium salt and the catalytic system (Pd(OAc)₂ + PPh₃) the cyclization of the same substrate 3 led only to compounds resulting from an initial Heck reaction of the vinyl bromide on the neighbouring olefin.

Wacker-type reaction - Heck reaction - palladium - trans-hydrindane - biquinane

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