生体模倣型オスミウム錯体を触媒とするアルケンの酸化的変換反応

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  • 杉本 秀樹
    大阪大学大学院工学研究科生命先端工学専攻
  • 伊東 忍
    大阪大学大学院工学研究科生命先端工学専攻

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タイトル別名
  • Oxidative Transformation of Alkenes Catalyzed by Bioinspired Osmium Complexes
  • セイタイ モホウガタ オスミウム サクタイ オ ショクバイ ト スル アルケン ノ サンカテキ ヘンカン ハンノウ

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<p>Metallo-enzymes catalyze a variety of chemical transformation reactions such as oxidation, reduction, coupling, and hydrolysis, most of which are essential for synthetic organic chemistry. Rieske dioxygenases, one of the most abundant nonheme iron enzyme family, catalyzes selective cis-dihydroxylation of arene C=C double bonds using molecular oxygen or hydrogen peroxide. The iron model complexes have so far been developed and employed in cis-dihydroxylation of alkenes as a catalyst. However, there are several drawbacks in the iron model systems such as stability, substrate limitation, low substrate and oxidant conversion, and low product selectivity. To make more efficient catalytic systems, the authors have developed osmium-complexes as the model compounds of the Rieske dioxygenase reaction center. Herein, the authors employ them as the catalyst for cis-dihydroxylation of alkenes. The active oxidant has been identified, and the catalytic mechanism has been explored based on the kinetic analysis and DFT calculations. Furthermore, the catalytic system has been applied to oxidative cyclization of 1,5-dienes to afford tetrahydrofuran derivatives and to aminohydroxylation of alkenes to give cis-1,2-aminoalcohols.</p>

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