Synthesis of optically active novel 1,1,2-trifluoro-1-alken-3-ols through lipase-catalyzed reaction

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2801-2802

  Takagi, Yumiko ^a   Kashiwagi, Masaya ^a   Kihara, Hiroshi ^a   Itoh, Toshiyuki ^b  

^a HYOGO UNIVERSITY OF TEACHER EDUCATION   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,2 TRICHLORO 1,2,2 TRIFLUOROETHANE; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; BURKHOLDERIA CEPACIA; CAPILLARY GAS CHROMATOGRAPHY; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; ESTERIFICATION; SYNTHESIS;

EID: 0033515872     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00298-1     Document Type: Article

References (16)

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11. The absolute configuration of the produced acetate has not yet been determinated, though we assume it to be (R) by the general enantiopreference of PCL; Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
12. (a)Takagi, Y.; Teramoto, J.; Itoh, T.; Kihara, H.; Tsukube, H. Tetrahedron Lett. 1996, 37, 4991.
13. (b)Takagi, Y.; Ino, R.; Itoh, T.; Kihara, H.; Tsukube, H. Chem. Lett. 1997, 1247. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem. 1997, 62, 9165.
14. (b)Takagi, Y.; Ino, R.; Itoh, T.; Kihara, H.; Tsukube, H. Chem. Lett. 1997, 1247. Itoh, T.; Mitsukura, K.; Kanphai, W.; Takagi, Y.; Kihara, H.; Tsukube, H. J. Org. Chem. 1997, 62, 9165.
15. Enatioselectivity was improved upto 100 by the addition of 5 mol% of the thiacrown ether when 1 b (R=Ph) was subjected to the reaction in the absence of BHT, though the recovered yield was significantly reduced by polymerization. On the contrary, no such effect was observed when the reaction was carried out in the presence of BHT.
16. The authors are grateful to the SC-NMR Laboratory of Okayama University for the NMR measurements. They also thank the Amano Pharmaceutical Co., Ltd, for providing the lipase.