Lipase-catalyzed efficient kinetic resolution of 3-Hydroxy-3-(pentafluorophenyl)propionitrile

Tetrahedron Letters

Volumn 38, Issue 11, 1997, Pages 1987-1990

  Sakal, Takashi ^a   Takayama, Tetsuo ^a   Ohkawa, Takafumi ^a   Yoshio, Osamu ^a   Ema, Tadashi ^a   Utaka, Masanori ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; PROPIONITRILE; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; FLUORINATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031575787     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00255-4     Document Type: Article

References (29)

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16. 9. Prepared by the addition of acetic anhydride before quenching the reaction and an additional stirring of the reaction mixture overnight at room temperature.
17. 2O (7.5 mL) (distilled from sodium) was stirred for the indicated time at 30 °C.
18. 11. TOYOBOLIP was suitably utilized in the resolution of the fluorinated substrate (see reference 5a).
19. 3) δ 81.23-81.68 (m, 2F), (t, J = 22.3Hz, 1F), 98.70-99.18 (m, 2F); IR (KBr) 3411 (OH), 2958 (CH), 2267 (CN).
20. 3) δ 81.40-81.82 (m, 2F), 90.87 (t, J = 22.3Hz, 1F), 100.28-100.72 (m, 2F); IR (neat) 2993 (CH), 2258 (CN), 1751 (C=O).
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22. 15. A mixture of (±)-2 (100 mg), lipase (entry 1-4: 100 mg, entry 5: 200 mg) and a phosphate buffer (pH 7.2, 5.0 mL), acetone (0.5 mL) was stirred for the indicated time at 30 °C.
23. 16. The selectivity was enhanced by use of phenylthioacetate as an acyl moiety (see references 1a and 1b).
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