An efficient method for the synthesis of 2′,3′-nonsubstituted cycloalkane-1,3-dione-2-spirocyclopropanes using (2-bromoethyl)-diphenylsulfonium trifluoromethanesulfonate

Hisanori Nambu*, Naoki Ono, Wataru Hirota, Masahiro Fukumoto, Takayuki Yakura

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)1763-1768
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume64
Issue number12
DOIs
StatePublished - 2016

Keywords

  • 1,3-cyclohexanedione
  • Cyclopropane
  • Double alkylation
  • Spiro compound
  • Sulfonium salt

ASJC Scopus subject areas

  • General Chemistry
  • Drug Discovery

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