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Volumn 61, Issue 7, 1996, Pages 2332-2336

Efficient synthesis of optically pure 1,1,1-trifluoro-2-alkanols through lipase-catalyzed acylation in organic media

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ORGANOFLUORINE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

EID: 0029995228     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951976a     Document Type: Article
Times cited : (50)

References (24)
  • 3
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    • (c) Nohira, H. J. Synth. Org. Chem., Jpn. 1991, 49, 467 and references cited therein.
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    • Nohira, H.1
  • 8
    • 4243794106 scopus 로고
    • Transesterification-based enzymatic resolution of secondary alcohols is now widely regarded as one of the best methods of choice for the synthesis of an enantiomer of an alcohol with high enantiomeric purity. For reviews see: (a) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (b) Faber, K.; Riva, S. Synthesis 1992, 895.
    • (1992) Chem. Rev. , vol.92 , pp. 1071
    • Santaniello, E.1    Ferraboschi, P.2    Grisenti, P.3    Manzocchi, A.4
  • 9
    • 4243794106 scopus 로고
    • Transesterification-based enzymatic resolution of secondary alcohols is now widely regarded as one of the best methods of choice for the synthesis of an enantiomer of an alcohol with high enantiomeric purity. For reviews see: (a) Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071. (b) Faber, K.; Riva, S. Synthesis 1992, 895.
    • (1992) Synthesis , vol.895
    • Faber, K.1    Riva, S.2
  • 10
    • 84889536395 scopus 로고    scopus 로고
    • note
    • The lithium salt of TFA could be kept at room temperature for several months, though it was a deliquescent compound.
  • 11
    • 84889510004 scopus 로고    scopus 로고
    • note
    • Vinyl acetate was found better as acyl donor than vinyl propionate in enantioselectivity
  • 12
    • 84889508425 scopus 로고    scopus 로고
    • note
    • List of lipases tested: Lipase PS (Pseudomonas cepacia), LPL (Pseudomonas aeruginosa), Lipase AK (Pseudomonas sp.), CAL (Candida antarctica), Lipase AY (Candida rugosa), CCL (Candida rugosa), Immobilized Lipase from Pseudomonas fluorescence, Lipase CES (Pseudomonas sp.) PPL (Porcine pancreas), PLE (Pig liver), Lipozyme (Mucor miehei), Lipase L (Candida lipolytica), Lipase A (Aspergillus niger), Lipase GC (Geotrichum candidum), Protease A, Lipase F (Rizopus javanicus), Lipase E (Penicillium roqueforti), Lipase N (Rhizopus niveus), Lipase CE (Humicola lanuginosa), Protease S, Lipase M (Mucor javanicus), Protease P, Lipase G (Penicillium sp.), and Lipase D (Rhizopus delemar).
  • 13
    • 0000858214 scopus 로고
    • Examples, see: (a) Sakurai, T.; Margolin, A. L.; Russell, A. J.; Klivanov, A. M J. Am. Chem. Soc. 1988, 110, 7236. (b) Parida, S., Dordick, J. S. Ibid. 1991, 113, 2253. (c) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (d) Kamat, S. Biotechnol. Bioengin. 1992, 40, 158. (e) Arroyo, M.; Sinisterra, J. V. J. Org. Chem. 1994, 59, 4410.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7236
    • Sakurai, T.1    Margolin, A.L.2    Russell, A.J.3    Klivanov, A.M.4
  • 14
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    • Examples, see: (a) Sakurai, T.; Margolin, A. L.; Russell, A. J.; Klivanov, A. M J. Am. Chem. Soc. 1988, 110, 7236. (b) Parida, S., Dordick, J. S. Ibid. 1991, 113, 2253. (c) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (d) Kamat, S. Biotechnol. Bioengin. 1992, 40, 158. (e) Arroyo, M.; Sinisterra, J. V. J. Org. Chem. 1994, 59, 4410.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2253
    • Parida, S.1    Dordick, J.S.2
  • 15
    • 33751385630 scopus 로고
    • Examples, see: (a) Sakurai, T.; Margolin, A. L.; Russell, A. J.; Klivanov, A. M J. Am. Chem. Soc. 1988, 110, 7236. (b) Parida, S., Dordick, J. S. Ibid. 1991, 113, 2253. (c) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (d) Kamat, S. Biotechnol. Bioengin. 1992, 40, 158. (e) Arroyo, M.; Sinisterra, J. V. J. Org. Chem. 1994, 59, 4410.
    • (1993) J. Org. Chem. , vol.58 , pp. 3238
    • Parida, S.1    Dordick, J.S.2
  • 16
    • 0027112426 scopus 로고
    • Examples, see: (a) Sakurai, T.; Margolin, A. L.; Russell, A. J.; Klivanov, A. M J. Am. Chem. Soc. 1988, 110, 7236. (b) Parida, S., Dordick, J. S. Ibid. 1991, 113, 2253. (c) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (d) Kamat, S. Biotechnol. Bioengin. 1992, 40, 158. (e) Arroyo, M.; Sinisterra, J. V. J. Org. Chem. 1994, 59, 4410.
    • (1992) Biotechnol. Bioengin. , vol.40 , pp. 158
    • Kamat, S.1
  • 17
    • 0027990305 scopus 로고
    • Examples, see: (a) Sakurai, T.; Margolin, A. L.; Russell, A. J.; Klivanov, A. M J. Am. Chem. Soc. 1988, 110, 7236. (b) Parida, S., Dordick, J. S. Ibid. 1991, 113, 2253. (c) Parida, S.; Dordick, J. S. J. Org. Chem. 1993, 58, 3238. (d) Kamat, S. Biotechnol. Bioengin. 1992, 40, 158. (e) Arroyo, M.; Sinisterra, J. V. J. Org. Chem. 1994, 59, 4410.
    • (1994) J. Org. Chem. , vol.59 , pp. 4410
    • Arroyo, M.1    Sinisterra, J.V.2


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