ジルコノセン錯体を用いた新規炭素-炭素結合形成反応の開発

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タイトル別名
  • Development of Novel Carbon-Carbon Bond Forming Reactions Using Zirconocene Complex
  • ジルコノセン サクタイ オ モチイタ シンキ タンソ タンソ ケツゴウ ケイセイ ハンノウ ノ カイハツ

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抄録

  Novel zirconium-mediated carbon-carbon bond-forming reactions were developed. The allylic, γ-alkoxyallylic, allenyl, and γ,γ-dialkoxyallylic zirconium species can be prepared from corresponding ethers under mild conditions through the addition of a zirconocene-butene complex to the carbon-carbon multiple bond of the ethers and subsequent β-elimination of the alkoxyl group. The γ,γ-dialkoxyallylic zirconium species reacts with carbonyl compounds at the β-position of the zirconium atom like a ketene dialkyl acetal in the presence of stoichiometric amounts of Lewis acid and gave cyclopropane and/or cyclobutane derivatives. Intramolecular reaction of allylic zirconium species with acetal also develops as a ring contraction reaction of carbohydrates and morpholine derivatives. This method is useful for the construction of chiral highly functionalized carbocycles and pyrrolidines. The intramolecular ester transfer reaction through the zirconium-mediated coupling reaction of alkenyl carbamates gave γ-aminobutyric acid derivatives and pyrrolidine-3-carboxylic acids.<br>

収録刊行物

  • 薬学雑誌

    薬学雑誌 123 (11), 933-948, 2003-11-01

    公益社団法人 日本薬学会

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