Favorskii Reaction of 2-Bromobicyclo[3.3.1]nonan-3-one

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概要

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• Both 2β-bromobicyclo[3.3.1]nonan-3-one (IIa) and its 2α- epimer (IIb) afforded methyl bicyclo[3.2.1]octane-6β-carboxylate (IIIa) stereoselectively in the Favorskii reaction using sodium methoxide in methanol. In the reaction using sodium methoxide in dimethoxyethane (DME) at room temperature, the stereoselectivity decreased and the product was contaminated with methyl bicyclo[3.2.1]octane-6α-carboxylate (IIIb). However, when the reaction in DME was carried out at 0℃, IIIa was the only product.The routes involved in these transformations were examined by using nuclear magnetic resonance spectroscopic techniques with the deuterated compounds.

• 社団法人日本薬学会の論文
• 1986-06-25

著者

• 山崎 高應

  Faculty of Pharmaceutical Sciences, University of Toyama

• 的場 勝英

  Faculty of Pharmaceutical Sciences, University of Toyama

• 山崎 高広

  富山医科薬科大学

• 村岡 修

  Faculty of Pharmaceutical Sciences, Kinki University

• 村岡 修

  Faculty Of Pharmaceutical Sciences Kinki University

• 山崎 高應

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 糸岡 利行

  Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University

• 百瀬 雄章

  Faculty of Pharmaceutical Sciences, Kinki University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Toyama Medical & Pharmaceutical University

• 的場 勝英

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  富山医薬大・薬

• 百瀬 雄章

  (present Address)faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Osaka University

• 百瀬 雄章

  Faculty Of Pharmaceutical Sciences Kanazawa University

• Muraoka O

  Shonai Regional Center For Plant Biotechnol. Yamagata

• 糸岡 利行

  Faculty Of Pharmaceutical Sciences Kinki University

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