Preparation and Lipase-catalyzed Optical Resolution of 2,2,2-Trifluoro-1-(naphthyl)ethanols

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概要

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• The optical resolution of racemic 2, 2, 2-trifluoro-1-(naphthyl)ethanols (TFNEs) was achieved by lipase-catalyzed enantioselective acetylation with vinyl acetate in octane, S-acetates and R-alcohols being obtained. The introduction of a methyl group into the naphthalene ring at the 4-position (2b) or the 2-position (2c) markedly decreased the reactivity, in particular for 2c. 2, 2, 2-Trifluoro-1-(1-naphthyl)ethanol (2a) behaved differently from the regio-isomer, 2, 2, 2-trifluoro-1-(2-naphthyl)ethanol (2d) : The enantioselectivity of lipases [LIP (Pseudomonas), PLC (Alcaligenes), and ALC (Achromobacter)] was high for 2a but low for 2d, whereas lipases [AK and PS (Pseudomonas)] exhibited higher selectivity for 2d than for 2a. Three other derivatives, 2, 2, 2-trifluoro-1-(phenyl)ethanol (2e), 2, 2, 2-trifluoro-1-(indol-3-yl)ethanol (2f), and 1-(1-naphthyl)ethanol (2g), were prepared, and their behaviors with respect to lipase-catalyzed acetylation were compared with 2a.

• 社団法人日本農芸化学会の論文
• 1995-02-23

著者

• KATO Katsuya

  Department of Materials Science and Engineering, Graduate School of Engineering, Nagoya University

• KATO Katsuya

  National Institute of Advanced Industrial Science and Technology (AIST)

• KIMOTO Hiroshi

  Department of lmmunology, National lnstitute of Health of Japan

• FUJII SHOZO

  Department of Chemistry, National Industrial Research Institute of Nagoya

• KATAYAMA MASATO

  Department of Chemistry, National Industrial Research Institute of Nagoya

• Fujii Shozo

  Department Of Chemistry National Industrial Research Institute Of Nagoya

• Katayama Masato

  Department Of Agricultural Chemistry Nagoya University

• Kimoto H

  National Institute Of Advanced Industrial Scienec And Technology (aist)

• Kimoto Hiroshi

  Department Of Immunology Japnese Institute Of Infectious Diseases

• Kato Katsuya

  National Industrial Research Insitute Of Nagoya

• Gautam K.

  Department of Chemistry, National Industrial Research Institute of Nagoya

• Katayama M

  Cooperative Research Laboratory For Plant Growth Regulator Development National Institute Of Advance

• Kato K

  National Institute Of Advanced Industrial Science And Technology (aist)

• Gautam K.

  Department Of Chemistry National Industrial Research Institute Of Nagoya

• Kato Katsuya

  Department Of Applied Biological Science Faculty Of Science And Technology Science University Of Tok

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