Synthesis of P-chiral, non-racemic phosphinylacetates via enzymatic resolution of racemates

被引：0
|
作者：
Kielbasinski, P
Zurawinski, R
Pietrusiewicz, KM
Zablocka, M
Mikolajczyk, M
机构：
[1] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland
[2] Marie Curie Sklodowska Univ, Dept Chem, PL-20031 Lublin, Poland
来源：
POLISH JOURNAL OF CHEMISTRY | 1998年 / 72卷 / 03期
关键词：
chiral phosphine oxides; enzymatic hydrolysis; kinetic resolution;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A series of racemic methyl phosphinylacetates was hydrolyzed in the presence of porcine liver esterase (PLE) under the kinetic resolution conditions to give the corresponding P-chiral phosphinylacetic acids and recovered esters in high enantiomeric purity (72-100% ee). The Jones' active site model was applied to explain the enantioselectivity of this reaction.
引用
收藏
页码：564 / 572
页数：9
相关论文
共 50 条
  • [41] Synthesis of chiral, non-racemic cyclopentenones from allylic hydroxy phosphonates.
    Spilling, CD
    Yan, BL
    Bandyopadhyay, S
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U367 - U368
  • [42] Stereoselective synthesis and resolution of P-chiral phosphine chalcogenides.
    Pietrusiewicz, KM
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1996, 109 (1-4) : 573 - 576
  • [43] Efficient preparation of chiral non-racemic sulfur compounds
    Minville, Joannie
    Girardin, Melina
    Spino, Claude
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (09) : 603 - 618
  • [44] Chiral, non-racemic α-hydroxyphosphonates and phosphonic acids via stereoselective hydroxylation of diallyl benzylphosphonates
    Skropeta, D
    Schmidt, RR
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (02) : 265 - 273
  • [45] Enzymes in organic chemistry, 11:: Hydrolase-catalyzed resolution of α- and β-hydroxyphosphonates and synthesis of chiral, non-racemic β-aminophosphonic acids
    Woschek, A
    Lindner, W
    Hammerschmidt, F
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (12) : 1287 - 1298
  • [46] Synthesis and electrospray mass spectrometric studies on a chiral, non-racemic, phosphoramide receptor molecule
    Smith, ARC
    Heck, AJR
    Kenny, JA
    Kettenes-van den Bosch, JJ
    Wills, M
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (17) : 3267 - 3271
  • [47] Recent developments in chiral non-racemic sulfinyl-group chemistry in asymmetric synthesis
    Hanquet, G
    Colobert, F
    Lanners, S
    Solladié, G
    [J]. ARKIVOC, 2003, : 328 - 401
  • [48] CHIRAL (NON-RACEMIC) 4-SUBSTITUTED QUINOLIZIDINES - SYNTHESIS AND CONFORMATIONAL-ANALYSIS
    MCINTOSH, JM
    MATASSA, LC
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 146 - ORGN
  • [49] Enantioselective synthesis of indolizidine and quinolizidine derivatives from chiral non-racemic bicyclic lactams
    Agami, C
    Dechoux, L
    Hebbe, S
    Ménard, C
    [J]. TETRAHEDRON, 2004, 60 (25) : 5433 - 5438
  • [50] AZAPROPELLANES .5. SYNTHESIS OF CHIRAL (NON-RACEMIC) 2-METHYL AZAPROPELLANES
    MCINTOSH, JM
    ACQUAAH, SO
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (07): : 1752 - 1756
12345