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Synlett 1995; 1995(12): 1257-1259
DOI: 10.1055/s-1995-5238
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Synthesis and Thermal Reactivity of Enyne Allene Esters. An Intramolecular [2+2] Cycloaddition as a New Mode of Cycloisomerization

Thomas Gillmann* , Thekla Hülsen, Werner Massa, Sigrid Wocadlo
  • *Institute für Pharmazeutische Chemie der Philipps-Universität Marburg, Marbacher Weg 6, 35032 Marburg, Germany, Fax +49-6421-287052; E-mail Gillmann@nws161.pharmazie.uni-marburg.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Enyne allene esters 4 and 5 were prepared under mild conditions using a Pd-catalyzed cross coupling reaction as the key step. Upon heating in the presence of 1,4-cyclohexadiene, 5 gave naphthalenes, while 4, in an unprecedented mode of cycloisomerization, was found to intramolecularly undergo a [2+2] cycloaddition leading to benzofulvene derivative 9.

intramolecular [2+2] cycloaddition - enyne allene esters - 2-haloallene esters - palladium-catalyzed cross coupling