Ring Opening of Cyclopropanemonocarboxylates and 1,1-Cyclopropanedicarboxylates Using Samarium(II) Diiodide (SmI_2)-HMPA-THF System

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概要

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• The cyclopropane ring in 2-substituted 1,1-cyclopropanedicarboxylates was regioselectively opened by using samarium(II) diiodide (SmI_2) in a hexamethylphosphoric triamide (HMPA)-tetrahydrofuran (THF) (1 : 10) system under mild and neutral conditions to give (2-substituted ethyl)malonates in moderate to good yields. The cyclopropane ring in 2-substituted cyclopropanecarboxylates or 2-substituted 3-(trimethylsilyl)cyclopropanecarboxylates was similarly cleaved regioselectively by using SmI_2 in a HMPA-THF (1 : 1) system to give 4-arylbutyrates or 4-aryl-3-(trimethylsilyl)butyrates in 16-89% yields. The reaction mechanism of these ring-opening reactions is discussed.

• 社団法人日本薬学会の論文
• 1995-12-15

著者

• 太田 俊作

  Kyoto Pharmaceutical University

• 山下 正行

  Kyoto Pharmaceutical University

• 川崎 郁勇

  Kyoto Pharmaceutical University

• 小川 和男

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 奥山 和典

  Kyoto Pharmaceutical University

• 大原 隆

  Kyoto Pharmaceutical University

• 酒井 清美

  Kyoto Pharmaceutical University

• 中田 幸子

  Kyoto Pharmaceutical University

• 川辺 登喜子

  Kyoto Pharmaceutical University

• 楠本 美紀

  Kyoto Pharmaceutical University

• 川崎 郁勇

  京都薬大

• 太田 俊作

  京都薬科大学薬学部

• Sakai Kiyomi

  Kyoto Pharmaceutical University

• 太田 俊作

  Kyoto College Of Pharmacy

• 山下 正行

  京都薬科大学薬学部

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