Lipase-catalyzed transesterification of 2-phenyl-1-propanol with vinyl esters having aromatic ring in acyl moiety

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5223-5226

  Kawasaki, Masashi ^a   Goto, Michimasa ^b   Kawabata, Shigeki ^a   Kodama, Tomoko ^b   Kometani, Tadashi ^b  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b TOYAMA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

Enantioselection; Enzymes and Enzyme reactions; Resolution

Indexed keywords

2 PHENYLPROPANOL; PROPRANOLOL DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ALCOHOL METABOLISM; ARTICLE; CATALYSIS; ENANTIOMER; ENZYME ACTIVITY; ESTERIFICATION;

EID: 0033538636     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00943-0     Document Type: Article

References (30)

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24. Although Chen et al. employed 5-phenylpentanoic acid in the lipase-catalyzed asymmetric esterification of 1-phenyl-1-ethanol, the reaction rate was too late to calculate the E value. See: Chen, C. -S.; Sih, C. J. Angew. Chem. Int. Ed. Eng. 1989, 28, 695-707.
25. Although Koshiro et al. employed either 5-phenylpentanoic acid or 11-phenylundecanoic acid in the lipase-catalyzed asymmetric esterification of menthol, the E values were not evaluated. See: Koshiro, S.; Sonomoto, K.; Tanaka, A.; Fukui, S. J. Biotechnol. 1985, 2, 47-57.
26. E = 9.8 for the transesterification with vinyl acetate, see: Chen, C. -S.; Liu, Y. -C. J. Org. Chem. 1991, 56, 1966-1968. E = 13 for the hydrolysis of the corresponding ester, see: Matsumoto, T.; Takeda, Y.; Iwata, E.; Sakamoto, M.; Ishida, T. Chem. Pharm. Bull. 1994, 42, 1191-1197.
27. E = 9.8 for the transesterification with vinyl acetate, see: Chen, C. -S.; Liu, Y. -C. J. Org. Chem. 1991, 56, 1966-1968. E = 13 for the hydrolysis of the corresponding ester, see: Matsumoto, T.; Takeda, Y.; Iwata, E.; Sakamoto, M.; Ishida, T. Chem. Pharm. Bull. 1994, 42, 1191-1197.
28. Lobell, M.; Schneide, M. P. Synthesis 1994, 375-377.
29. The resolution of (=)-1 was also carried out at 30 °C. For example, E value with vinyl 3-phenylpropanoate (E = 18) was six times larger than that with vinyl acetate (E = 3). This ratio was almost the same value as that at 10 °C. However, some reactions proceeded very fast at 30 °C. Therefore, we decided to evaluate the resolution at 10 °C more exactly.
30. Although an initial rate should be determined using pure enantiomers, we used the rates calculated from the racemic 2-phenyl-1-propanol results. Therefore, the relative rates are rough relative initial rates.