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Synlett 1996; 1996(2): 145-146
DOI: 10.1055/s-1996-5359
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Palladium(0)-Catalyzed Cyclization of 6-(2-Alkenyl)-2,7-octadienyl Acetates with Novel Diastereofacial Selection

Takayuki Doi, Arata Yanagisawa, Takashi Takahashi, Keiji Yamamoto*
  • *Department of Chemical Engineering, Tokyo Institute of Technology, Ookayama, Meguro, Tokyo 162, JAPAN
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Publication Date:
31 December 2000 (online)

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Palladium(0)-catalyzed cyclization of 6-(2-alkenyl)-2,7-octadienyl acetates (1) was carried out. When the 6-substituent is an allyl group, tandem cyclization of 1a has occurred to give trans-bicyclo[3.3.0]octane 2a. The compounds 1b-d having (E)- or (Z)-2-alkenyl groups at 6-position underwent the cyclization leading to 3b-d, which resulted from β-elimination of the common 2-vinylcyclopentylmethylpalladium intermediates. There was found an unprecedented cis diastereoselection at C(3)-C(6) of 1 during the cyclization as well as trans diastereoselection at C(6)-C(7) in the particular formation of 2a.

palladium(0) catalyst - cyclization - diastereofacial selection

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