Synlett 2008(7): 1071-1075  
DOI: 10.1055/s-2008-1042919
LETTER
© Georg Thieme Verlag Stuttgart · New York

Tandem [2+1] Cycloaddition-Ring Expansion of Bicyclic Alkenes with Tertiary Propargylic Acetates Catalyzed by Palladium(II)-Coordinated Phosphinous Acid

Julie Bigeaulta, Innocenzo de Riggia, Yves Gimbertb, Laurent Giordano*a, Gérard Buono*a
a Université d’Aix-Marseille, ECM, Institut des Sciences Moléculaires de Marseille (ISM2), CNRS UMR 6263; Avenue Escadrille ­Normandie Niemen, Case A 62, 13397 Marseille Cedex 20, France
Fax: +33(491)282742; e-Mail: gerard.buono@univ-cezanne.fr; e-Mail: laurent.giordano@univ-cezanne.fr;
b Université Joseph Fourier de Grenoble, Département de Chimie Moléculaire, UMR CNRS 5250, ICMG FR-2607, 38041 Grenoble Cedex 9, France
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Publikationsverlauf

Received 22 December 2007
Publikationsdatum:
17. März 2008 (online)

Abstract

Palladium-SPO complex catalyzed the tandem [2+1] cycloaddition-ring expansion of norbornene derivatives with tertiary propargylic acetates to afford bicyclo[3.2.1]octadienes.

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Reaction carried out without Pd(OAc)2/CyPhP(O)H as a catalytic system did not proceed at all.