Stereochemical studies of the hydrogenation with an asymmetrically modified Raney nickel catalyst. The hydrogenation of acetylacetone.

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概要

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• The hydrogenation of acetylacetone (I) over asymmetrically modified Raney nickel (MRNi) proceeded, step by step, as follows: acetylacetone (I)\oversetStep 1→ 4-hydroxy-2-pentanone (II) \oversetStep 2→ 2,4-pentanediol (III). It was demonstrated that the optical yield of Step 1 and the diastereomer excess of Step 2 are governed by the ratio of the stereo-differentiating reaction site to the non-stereo-differentiating reaction site on the catalyst. The stereochemistry of each step was also discussed based on the mode of the intermolecular hydrogen bondings between the substrate and tartaric acid adsorbed on the catalyst. RNi modified with a mixture of tartaric acid and NaBr (TA–NaBr–MRNi) gave the best result with respect to both Step 1 and Step 2.

• 公益社団法人 日本化学会の論文

著者

• Tai Akira

  Institute For Protein Research Osaka University

• Harada Tadao

  Institute for Protein Research, Osaka University

• Ito Kazuhisa

  Institute for Protein Research, Osaka University

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