An Efficient Method for the Synthesis of 2′,3′-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

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  • Nambu Hisanori
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama
  • Ono Naoki
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama
  • Hirota Wataru
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama
  • Fukumoto Masahiro
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama
  • Yakura Takayuki
    Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama

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  • An Efficient Method for the Synthesis of 2',3'-Nonsubstituted Cycloalkane-1,3-dione-2-spirocyclopropanes Using (2-Bromoethyl)diphenylsulfonium Trifluoromethanesulfonate

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Abstract

<p>An efficient and practical synthesis of 2′,3′-nonsubstituted cyclohexane-1,3-dione-2-spirocyclopropanes using a sulfonium salt was achieved. The reaction of 1,3-cyclohexanediones and (2-bromoethyl)diphenylsulfonium trifluoromethanesulfonate with powdered K2CO3 in EtOAc at room temperature (r.t.) provided the corresponding spirocyclopropanes in high yields. The synthetic method was also applied to 1,3-cyclopentanedione, 1,3-cycloheptanedione, 1,3-indanedione, acyclic 1,3-diones, ethyl acetoacetate, and Meldrum’s acid.</p>

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