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Volumn 37, Issue 28, 1996, Pages 5001-5002

Simple preparation of optically pure bis(trifluoromethyl)alkanediols through lipase-catalyzed reaction

Author keywords

[No Author keywords available]

Indexed keywords

ACETOACETIC ACID; TRIACYLGLYCEROL LIPASE;

EID: 15844366018     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00994-X     Document Type: Article
Times cited : (16)

References (9)
  • 5
    • 0003047802 scopus 로고
    • A* phase, while liquid crystals prepared from 3 with even number of n exhibited SmC* and SmA phase
    • A* phase, while liquid crystals prepared from 3 with even number of n exhibited SmC* and SmA phase.
    • (1995) Chem. Lett. , pp. 719-720
    • Suzuki, Y.1    Isozaki, T.2    Kusumoto, T.3    Hiyama, T.4
  • 6
    • 0001939466 scopus 로고
    • 3) Preparation of 96%ee of (trifluoromethyl)oxirane was reported recently through enantioselective reduction of 1,1,1-trifluoro-3-chloro-2-propanone by chlorodisiopinocamphenylborane: Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org.Chem. 1995, 60, 41-46.
    • (1995) J. Org.chem. , vol.60 , pp. 41-46
    • Ramachandran, P.V.1    Gong, B.2    Brown, H.C.3
  • 8
    • 85030209540 scopus 로고    scopus 로고
    • note
    • 5) CAL has the highest acylation efficiency of 1,1,1-trifluoro-2-alkanols among 25 types of commercial enzymes. For preparing optically active 1,1,1-trifluoro-2-nonanol, the trans-esterification method gave the product with better %ee than hydrolysis of the corresponding acetate in 0.1 M phosphate buffer at pH7.2, though the hydrolysis reaction proceeded more speedily than trans-esterification. See ref. 4. We re-examined CAL-catalyzed hydrolysis of 1,1,1-trifluoro-2-nonyl acetate under the present mixed solvent system, and found that hydrolyzed alcohol formed in an optically pure state with good yield. The mixed solvent system seemed effective to suppress non-enzymatic hydrolysis reaction of the acetate. Therefore, perfect resolution of 1,1,1-trifluoro-2-alkanols was achieved by both hydrolysis-and trans-esterification methods using CAL.
  • 9
    • 0030575397 scopus 로고    scopus 로고
    • note
    • (S,S) = 23.1 min. Assignment was carried out by comparing the authentic samples derived from commercial 75%ee of (S)-3,3,3-trifluoro-1,2-epoxypropane. Tetrahedron Letters, Vol. 37, No. 28, pp. 5003-5006, 1996


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.