Iodide-Catalyzed Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes

• Nambu, Hisanori

• onuki, yuta

• Ono, Naoki

• Yakura, Takayuki

抄録

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The ring-opening cyclization of 2',3'-nonsubstituted and 2'-electron-withdrawing group (EWG)-substituted cyclohexane-1,3-dione-2-spirocyclopropanes was accomplished using iodide as a catalyst. The nonsubstituted derivatives afforded 3,5,6,7-tetrahydro-1-benzofuran-4(2H)-ones in high yields in the presence of trimethylsilyl iodide at room temperature. The EWG-substituted spirocyclopropanes, in turn, underwent regioselective ring opening followed by cyclization, which gave rise to 2-substituted tetrahydrobenzofuran-4-ones when a combination of tetrabutylammonium iodide catalyst and trifluoromethanesulfonic acid was used, whereas calcium iodide afforded the 3-substituted derivatives.

Article

収録刊行物

• Advanced Synthesis and Catalysis

  Advanced Synthesis and Catalysis 360 (15), 2938-2944, 2018-06-13

キーワード

• iodide catalysts
• cyclopropanes
• ring opening
• cyclization
• benzofurans

詳細情報

• CRID: 1050001202452888704
• NII論文ID: 120006643712
• ISSN: 16154169
• HANDLE: 10110/00019280
• Web Site: https://toyama.repo.nii.ac.jp/records/16834
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles