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Synlett 1999; 1999(5): 647-649
DOI: 10.1055/s-1999-2696
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A New Method for the Synthesis of Medium- and Large-Sized Carbocycles

Keiichi Masuya1 , Keiji Tanino, Isao Kuwajima2
  • 1Department of Chemistry, Tokyo Institut of Technology, Meguro, Tokyo 152-8551, Japan
  • 2The Kitasato Institute, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan
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Publikationsdatum:
31. Dezember 1999 (online)

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A new synthetic method for medium and large-sized carbocycles has been developed. An acyclic compound having an olefin moiety and a 3-(methylthio)allyl acetate moiety at each of the terminal positions was designed as a cyclization precursor. The corresponding allyl cation intermediate, which was generated by treatment with EtAlCl2, underwent cyclization via an intramolecular addition reaction. The ring size of the product, which depends on the reaction site of the allyl cation, can be controlled by changing the nucleophilicity of the terminal olefin moiety.

cyclization - allylcation - Lewis acid - vinyl sulfide - homoallylsilane