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Synlett 1999; 1999(S1): 951-953
DOI: 10.1055/s-1999-3087
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Construction of Eight-Membered Carbocycles by Palladium-Catalyzed [4 + 4] Cycloaddition of Vinylallenes

Masahiro Murakami* , Kenichiro Itami, Yoshihiko Ito
  • *Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Yoshida, Kyoto 606-8501, Japan; Fax +81-75-7 53-56 68
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Publication Date:
31 December 1999 (online)

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A palladium-catalyzed [4 + 4] cycloaddition reaction is described. A vinylallene having a pendant phenyl or vinyl substituent was treated with a catalytic amount of a palladium(O) complex to afford a symmetrical eight-membered carbocycle. The extended conjugation of the diene unit of an intermediate with the pendant unsaturated substituent is important for the [4 + 4] cycloaddition to occur.

[4 + 4] cycloaddition - carbocycles - eight-membered ring - palladium - vinylallenes