Preparation and lipase-catalyzed optical resolution of 2,2,2-trifluoro-1-(1-naphthyl)ethanols

• Kato Katsuya

• Katayama Masato

• Gautam K. Rakesh

• Fujii Shozo

• Kimoto Hiroshi

書誌事項

タイトル別名

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

抄録

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.

収録刊行物

• Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ

  Ｂｉｏｓｃｉｅｎｃｅ，　Ｂｉｏｔｅｃｈｎｏｌｏｇｙ，　ａｎｄ　Ｂｉｏｃｈｅｍｉｓｔｒｙ 59 (2), 271-276, 1995

  公益社団法人 日本農芸化学会

キーワード

• Organic Chemistry
• Molecular Biology
• Applied Microbiology and Biotechnology
• General Medicine
• Biochemistry
• Analytical Chemistry
• Biotechnology

詳細情報

• CRID: 1390282681450819840
• NII論文ID: 110002677423
• NII書誌ID: AA10824164
• DOI: 10.1271/bbb.59.271
• COI: 1:CAS:528:DyaK2MXktFGjuro%3D
• ISSN: 13476947
• ISSN: 09168451
• Web Site: http://www.tandfonline.com/doi/pdf/10.1271/bbb.59.271
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可