Optical resolution of 2,2,2-trifluoro-1-(9-phenanthryl)ethanol via enzymatic alcoholysis of its activated ester

• Published in: Journal of fermentation and bioengineering Vol. 81; no. 3; pp. 206 - 211
• Main Authors: Kato, Katsuya, Katayama, Masato, Fujii, Shozo, Fukaya, Haruhiko, Kimoto, Hiroshi
• Format: Journal Article
• Language: English
• Published: Osaka Elsevier B.V 1996; Society for Fermentation and Bioengineering
• Subjects: Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; enantioselective alcoholysis; Fundamental and applied biological sciences. Psychology; lipase; Methods. Procedures. Technologies; optical resolution; Pseudomonas aeruginosa; TFPE; TFAE; optical resolution; enantioselective alcoholysis; TFNE; lipase; Pseudomonadales; Enantioselectivity; Haloalcohol; Enzyme; Triacylglycerol lipase; Esterases; Carboxylic ester hydrolases; Alcoholysis; Ester; Optical resolution; Bacteria; Hydrolases; Pseudomonadaceae; Pseudomonas aeruginosa; Secondary alcohol; Enzymatic reaction
• ISSN: 0922-338X
• DOI: 10.1016/0922-338X(96)82209-4

Practical lipase LIP ( Pseudomonas aeruginosa)-catalyzed optical resolution of 2,2,2-trifluoro-1-(9-phenanthryl)ethanol (TFPE), which is a sterically hindered secondary alcohol, has been performed. The method was used effectively for the first enzymatic preparation of both enantiomers of TFPE via lipase-catalyzed enantioselective alcoholysis of its chloroacetate ester. A simple procedure was developed for separating the S-alcohol product from the unreactive R-chloroacetate ester and for hydrolyzing the latter to obtain the R-alcohol. Using a similar procedure, the optical resolution of 2,2,2-trifluoro-1-(1-naphthyl)ethanol (TFNE) was achieved as well.