Preparation of homochiral (S)- and (R)-1-(2-furyl)ethanols by lipase-catalyzed transesterification

被引:26
作者
Kaminska, J
Gornicka, I
Sikora, M
Gora, J
机构
[1] Institute of General Food Chemistry, Tech. Univ. of Łodz, 90-924 Łódź
关键词
D O I
10.1016/0957-4166(96)00088-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
1-(2-Furyl)ethanol 1 was resolved by irreversible transesterification with vinyl acetate using Lipozyme IM or Porcine Pancreas Lipase (PPL) in an organic solvent. (S)-alcohol (99% e.e.) was obtained in 80-85% yield using Lipozyme IM in carbon tetrachloride while (R)-1-(2-furyl)ethyl acetate (96% e.e.) in 75-80% yield resulted from transesterification using Lipozyme IM in hexane or PPL in tetrahydrofuran. (C) 1996 Elsevier Science Ltd
引用
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页码:907 / 910
页数:4
相关论文
共 15 条
[1]  
ACHMATOWICZ O, 1981, ORGANIC SYNTHESIS TO, P307
[2]   LACTOBACILLUS-KEFIR ALCOHOL-DEHYDROGENASE - A USEFUL CATALYST FOR SYNTHESIS [J].
BRADSHAW, CW ;
HUMMEL, W ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1532-1536
[3]   ASYMMETRIC REDUCTIONS OF KETONES USING LITHIUM ALUMINUM-HYDRIDE MODIFIED WITH N,N-DIALKYL DERIVATIVES OF (R)-(-)-2-AMINOBUTAN-1-OL [J].
BROWN, E ;
PENFORNIS, A ;
BAYMA, J ;
TOUET, J .
TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :339-342
[4]   ROLE OF SOLVENTS IN THE CONTROL OF ENZYME SELECTIVITY IN ORGANIC MEDIA [J].
CARREA, G ;
OTTOLINA, G ;
RIVA, S .
TRENDS IN BIOTECHNOLOGY, 1995, 13 (02) :63-70
[5]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[6]   CHEMOENZYMIC SYNTHESIS OF CHIRAL FURAN-DERIVATIVES - USEFUL BUILDING-BLOCKS FOR OPTICALLY-ACTIVE STRUCTURES [J].
DRUECKHAMMER, DG ;
BARBAS, CF ;
NOZAKI, K ;
WONG, CH ;
WOOD, CY ;
CIUFOLINI, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1607-1611
[7]  
FUELLING G, 1990, OPPORTUNITIES BIOTRA, P186
[8]   SPECIFICITIES OF ENZYMES CORRECTED FOR SOLVATION DEPEND ON THE CHOICE OF THE STANDARD STATE [J].
JANSSEN, AEM ;
HALLING, PJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) :9827-9830
[9]   RESOLUTION OF SECONDARY ALCOHOLS BY ENZYME-CATALYZED TRANSESTERIFICATION IN ALKYL CARBOXYLATES AS THE SOLVENT [J].
JANSSEN, AJM ;
KLUNDER, AJH ;
ZWANENBURG, B .
TETRAHEDRON, 1991, 47 (36) :7645-7662
[10]   SYNTHESIS OF OPTICALLY-ACTIVE 2-FURYLMETHANOLS AS USEFUL CHIRAL BUILDING-BLOCKS AND ITS APPLICATION TO THE SYNTHESIS OF (5R,6S)-6-ACETOXYHEXADECAN-5-OLIDE AND (+)-DISPARLURE [J].
KAMETANI, T ;
TSUBUKI, M ;
TATSUZAKI, Y ;
HONDA, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :639-646