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Synlett 1996; 1996(2): 157-158
DOI: 10.1055/s-1996-5361
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A New Synthetic Method for Cyclopentanones via Formal [3+2] Cycloaddition Reaction

Keiichi Masuya Kei Domon, Keiji Tanino, Isao Kuwajima*
  • *Department of Chemistry, Tokyo Institute of Technology, Meguro, Tokyo 152, Japan
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Publication Date:
31 December 2000 (online)

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A new synthetic method for cyclopentanone derivatives via formal [3+2] cycloaddition reaction of 2-oxyallyl cation and an alkene was developed. Under the influence of EtAlCl2 or AlCl3, 3-acetoxy-1-(methylthio)-2-(triisopropylsiloxy)-2-tridecene reacted with various kinds of alkenes to afford 2-(methylthio)cyclopentanone derivatives in good yield. The reaction was highly regioselective to yield the sterically more hindered regioisomer, which indicates that the initial C-C bond formation reaction between an alkene and the (1-(methylthio)-2-siloxy)allyl cation intermediate occurs at the γ-position of sulfur.

alkenyl sulfide - enol ether - cyclopentanone - cycloaddition - 2-oxyallyl cation