マグネシウムカルベノイドの化学の開拓と有機合成への応用

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  • 佐藤 毅
    東京理科大学大学院総合化学研究科総合化学専攻

書誌事項

タイトル別名
  • Exploitation of the Chemistry of Magnesium Carbenoids and Their Use in Organic Synthesis
  • マグネシウム カルベノイド ノ カガク ノ カイタク ト ユウキ ゴウセイ エ ノ オウヨウ

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説明

  Synthetic organic chemistry is a base of medicinal chemistry and the exploitation of new methods for carbon-carbon bond formation is of most importance in synthetic organic chemistry. Carbenes and carbenoids have long been known to be highly reactive carbon species that show a variety of unique reactivity. However, those reactive species are not fully used in organic synthesis. The reasons are as follows: one is the precursors for the generation of carbenes and carbenoids are quite limited and the other is that the reactivity of the species is too high to control. In order to solve the problem mentioned above, we used α-haloalkyl (or alkenyl) aryl sulfoxides as the precursors and used sulfoxide-magnesium exchange reaction for generation of much mild magnesium carbenoids. α-Haloalkyl (or alkenyl) aryl sulfoxides are quite easily synthesized in high overall yields. Magnesium carbenoids, cyclopropylmagnesium carbenoids, cyclobutylmagnesium carbenoids, magnesium β-oxido carbenoids, and magnesium alkylidene carbenoids are generated at low temperature from the corresponding sulfoxides with a Grignard reagent in quantitative yields. They were found to be stable usually at below -60°C for at least 30 min. The each magnesium carbenoids have their own unique reactivities and we could find many unprecedented reactions from these reactive species. Recent results for the developments of new synthetic methods based on the chemistry of magnesium carbenoids are described.<br>

収録刊行物

  • 薬学雑誌

    薬学雑誌 129 (9), 1013-1023, 2009-09-01

    公益社団法人 日本薬学会

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