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Synlett 1994; 1994(3): 191-193
DOI: 10.1055/s-1994-22790
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Sequential Heck and Diels-Alder Reactions: Facile Construction of Bicyclic Systems in a Single Synthetic Operation

Frank E. Meyer* , Kiah How Ang, Arno G. Steinig, Armin de Meijere
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany
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Publication Date:
22 March 2002 (online)

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Under catalytic conditions, (3.5 mol% Pd(OAc)2, 1.2 equiv. Ag2CO3 in acetonitrile) 2-bromo-1,6-diene 6 furnishes bis (exomethylene)cyclopentane 7. When generated in the presence of a dienophile, 7 immediately undergoes a Diels-Alder reaction; [4+2]-cycloadducts of 7 were thus prepared with a variety of dienophiles in a one-pot procedure in high yields.