The preparation of optically pure 3-hydroxyalkanoic acid. The enantioface-differentiating hydrogenation of the C=O double bond with modified Raney nickel. XXXVII.

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概要

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• The enantioface-differentiating hydrogenation of methyl 3-oxoalkanoate (CH<SUB>3</SUB>(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>COCH<SUB>2</SUB>COOCH<SUB>3</SUB>, <I>n</I>=0, 6, 8, 10, 12) over the (<I>R</I>,<I>R</I>)-tartaric acid–NaBr–modified Raney nickel catalyst ((<I>R</I>,<I>R</I>)-TA–NaBr–MRNi) gave methyl (<I>R</I>)-3-hydroxyalkanoate (CH<SUB>3</SUB>(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>CH(OH)CH<SUB>2</SUB>COOCH<SUB>3</SUB>, <I>n</I>=0, 6, 8, 10, 12) in an average optical yield of 85%. After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (<I>R</I>)-3-hydroxyalkanoic acid (CH<SUB>3</SUB>(CH<SUB>2</SUB>)<I><SUB>n</SUB></I>CH(OH)CH<SUB>2</SUB>COOH, <I>n</I>=0, 6, 8, 10, 12) in a reasonable yield. From the hydrogenation product with (<I>S</I>,<I>S</I>)-TA–NaBr–MRNi, optically pure (<I>S</I>)-3-hydroxyalkanoic acid was obtained by the same process as above.

• 公益社団法人 日本化学会の論文

著者

• Tai Akira

  Institute For Protein Research Osaka University

• OZAKI Hiroshi

  Institute for Protein Research, Osaka University

• Nakahata Masaaki

  Institute for Protein Research, Osaka University

• Imaida Motomasa

  Institute for Protein Research, Osaka University

• Harada Tadao

  Institute for Protein Research, Osaka University

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