Enzymatic kinetic resolution of 1-(3′-furyl)-3-buten-1-ol and 2-(2′-furyl)-propan-1-ol

被引：19
|
作者：
Bierstedt, A
Stölting, J
Fröhlich, R
Metz, P
机构：
[1] Tech Univ Dresden, Inst Organ Chem, D-01069 Dresden, Germany
[2] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2002年 / 12卷 / 24期
关键词：
D O I：
10.1016/S0957-4166(02)00023-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The enzymatic kinetic resolution of the racemic alcohols 1-(3'-furyl)-3-buten-1-ol(+/-)-1 and 2-(2'-furyl)propan-1-ol (+/-)-2 was investigated by screening a range of lipases and esterases for enantioselective transacylation, as well as for enantioselective hydrolysis. For both alcohols, lipase-catalyzed hydrolysis of the derived racemic acetate gave the best results for accessing the desired (S)-enantiomers. In the case of the secondary alcohol (+/-)-1 ASL turned out to be the optimum enzyme, whereas PPL was found to be superior in the case of the primary alcohol (+/-)-2. Additionally, an alternative access to (S)-2 via Oppolzer's camphor sultam methodology is described. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3399 / 3407
页数：9
相关论文
共 50 条
  • [41] 2-(4-Methylphenyl)-1-(phenylsulfonyl)propan-2-ol
    Shi, Bao-Jun
    Huang, Liang-Zhu
    Li, You-Qiang
    Si, Chang-Mei
    Du, Zhen-Ting
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2845 - +
  • [42] Kinetics of the reactions of Cl atoms with 2-buten-1-ol, 2-methyl-2-propen-1-ol, and 3-methyl-2-buten-1-ol as a function of temperature
    Rodriguez, Diana
    Rodriguez, Ana
    Soto, Amparo
    Aranda, Alfonso
    Diaz-de-Mera, Yolanda
    Notario, Alberto
    JOURNAL OF ATMOSPHERIC CHEMISTRY, 2008, 59 (03) : 187 - 197
  • [43] Calorimetric and computational study of 3-buten-1-ol and 3-butyn-1-ol.: Estimation of the enthalpies of formation of 1-alkenols and 1-alkynols
    Vélez, E
    Quijano, J
    Gaviria, J
    Roux, MV
    Jiménez, P
    Temprado, M
    Martín-Valcárcel, G
    Pérez-Parajón, J
    Notario, R
    JOURNAL OF PHYSICAL CHEMISTRY A, 2005, 109 (34): : 7832 - 7838
  • [44] Kinetics of the reactions of Cl atoms with 2-buten-1-ol, 2-methyl-2-propen-1-ol, and 3-methyl-2-buten-1-ol as a function of temperature
    Diana Rodriguez
    Ana Rodriguez
    Amparo Soto
    Alfonso Aranda
    Yolanda Diaz-de-Mera
    Alberto Notario
    Journal of Atmospheric Chemistry, 2008, 59 : 187 - 197
  • [45] SYNTHESIS OF 2-FLUORO-3-BUTEN-1-OL
    ROBINSON, CY
    JOHN, V
    JOURNAL OF FLUORINE CHEMISTRY, 1993, 62 (2-3) : 283 - 287
  • [46] Density and viscosity of binary mixtures of ethyl acetate with methanol, ethanol, propan-1-ol, propan-2-ol, butan-1-ol, 2-methylpropan-1-ol, and 2-methylpropan-2-ol at (298.15, 303.15, and 308.15) K
    Nikam, PS
    Mahale, TR
    Hasan, M
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1996, 41 (05): : 1055 - 1058
  • [47] Synthesis of (1R,2S)-2-(4′-allyl-2′,6′-dimethoxyphenoxyl)-1-(4"-hydroxy-3", 5"-dimethoxyphenyl)propan-1-ol
    Ding, Junwei
    Qi, Rongwei
    Zhou, Haitang
    Jiao, Bin
    Xia, Yamu
    JOURNAL OF CHEMICAL RESEARCH, 2011, (09) : 519 - 521
  • [48] Excess Molar Volumes of 1,3-Diethyl Propanedioate with Methanol, Ethanol, Propan-1-ol, Propan-2-ol, Butan-2-ol, 2-Methyl-propan-1-ol, and Pentan-1-ol at T = (288.15, 298.15, 313.15, and 328.15) K
    Wang, Yihe
    Yan, Weidong
    JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2010, 55 (09): : 4029 - 4032
  • [49] Transfer hydrogenation of ketones catalyzed by complexes of ruthenium(II) with the heterotridentate [P,N,O] ligands (S)-2-[{2-(diphenylphosphanyebenzylidene}amino]propan-1-ol, (S)-2-[{2-(diphenylphosphanyl)benzyl}amino]propan-1-ol or the [P,N,S] ligand (S)-2-(dimethylamino)-1-(diphenylphosphino)-3-(methylthio)propane
    Obaid, Abeer H.
    Stracey, Nuru G.
    Incarvito, Christopher D.
    Mercado, Brandon Q.
    Parr, Jonathan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 830 : 74 - 84
  • [50] Preparation and synthetic applications of lithiated vinyl sulfones derived from 3-buten-1-ol and 4-penten-1-ol
    Caturla, F
    Najera, C
    TETRAHEDRON, 1997, 53 (33) : 11449 - 11464
12345