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
  • [21] Convenient synthesis of chiral non-racemic S-mesityl sulfinimines
    Sasraku-Neequaye, Leonid
    MacPherson, David
    Stockman, Robert A.
    TETRAHEDRON LETTERS, 2008, 49 (07) : 1129 - 1132
  • [22] ENANTIOSELECTIVE SYNTHESIS OF NON-RACEMIC CHIRAL MOLECULES ON AN INDUSTRIAL-SCALE
    SCOTT, JW
    TOPICS IN STEREOCHEMISTRY, 1989, 19 : 209 - 226
  • [23] Organocatalyzed synthesis of chiral non-racemic 1,4-dihydropyridazines
    Pitacco, Giuliana
    Attanasi, Orazio A.
    De Crescentini, Lucia
    Favi, Gianfranco
    Felluga, Fulvia
    Forzato, Cristina
    Mantellini, Fabio
    Nitti, Patrizia
    Valentin, Ennio
    Zangrando, Ennio
    TETRAHEDRON-ASYMMETRY, 2010, 21 (05) : 617 - 622
  • [24] Synthesis of novel chiral non-racemic substituted trianglimine and trianglamine macrocycles
    Kuhnert, N
    Lopez-Periago, AM
    TETRAHEDRON LETTERS, 2002, 43 (18) : 3329 - 3332
  • [25] Enzymatic reactions in ionic liquids:: lipase-catalysed kinetic resolution of racemic, P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides
    Kielbasinski, P
    Albrycht, M
    Luczak, J
    Mikolajczyk, M
    TETRAHEDRON-ASYMMETRY, 2002, 13 (07) : 735 - 738
  • [26] Synthesis and resolution of a new P-chiral hydroxy phosphine
    Albert, J
    Cadena, JM
    Delgado, S
    Granell, J
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 603 (02) : 235 - 239
  • [27] Preparation of Novel Chiral Non-Racemic Diselenides and Applications in Asymmetric Synthesis
    Zhao, Liwei
    Li, Zhong
    Wirth, Thomas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (01) : 176 - 182
  • [28] A CONVENIENT SYNTHESIS OF HEXACARBONYLDICOBALT COMPLEXES OF CHIRAL (NON-RACEMIC) TERMINAL ALKOXYACETYLENES
    BERNARDES, V
    VERDAGUER, X
    MOYANO, A
    PERICAS, MA
    RIERA, A
    GREENE, AE
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 470 (1-2) : C12 - C14
  • [29] Synthesis and resolution of benzylisopropylphenylphosphine a monodentate P-chiral ligand
    Albert, J
    Bosque, R
    Cadena, JM
    Granell, JR
    Muller, G
    Ordinas, JI
    TETRAHEDRON-ASYMMETRY, 2000, 11 (16) : 3335 - 3343
  • [30] Enantioselective diethylzinc addition to aldehydes via chiral, non-racemic β-hydroxysalicylhydrazone catalysts
    Parrott, Raleigh W., II
    Dore, Delvis D.
    Chandrashekar, Seshanand P.
    Bentley, Jeromy T.
    Morgan, Brittany S.
    Hitchcock, Shawn R.
    TETRAHEDRON-ASYMMETRY, 2008, 19 (05) : 607 - 611
12345