Enzymatic reactions in ionic liquids:: lipase-catalysed kinetic resolution of racemic, P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides

被引：68

作者：

Kielbasinski, P ^{[1
]}

Albrycht, M ^{[1
]}

Luczak, J ^{[1
]}

Mikolajczyk, M ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 07期

关键词：

D O I：

10.1016/S0957-4166(02)00167-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Lipase-mediated acetylation of racemic P-chiral hydroxymethanephosphinates and hydroxymethylphosphine oxides was performed in ionic liquids under kinetic resolution conditions. Lipase AK (Amano) and lipase from Pseudomonas fluorescens (Fluka) were up to six times more enantioselective in BMIM-PF6, solutions than in common organic solvents. On the contrary, the analogous reactions performed in BMIM-BF4, were practically non-stereoselective. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：735 / 738

页数：4

共 22 条

[1] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
CHEN, CS
FUJIMOTO, Y
GIRDAUKAS, G
SIH, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
[2] New procedures for the resolution of chiral tert-butylphenylphosphine oxide and some of its reactions
Drabowicz, J
Lyzwa, P
Omelanczuk, J
Pietrusiewicz, KM
Mikolajczyk, M
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (14) : 2757 - 2763
[3] Enzymatic catalysis of formation of Z-aspartame in ionic liquid -: An alternative to enzymatic catalysis in organic solvents
Erbeldinger, M
Mesiano, AJ
Russell, AJ
[J]. BIOTECHNOLOGY PROGRESS, 2000, 16 (06) : 1129 - 1131
[4] STRUCTURE OF 1-ETHYL-3-METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE - MODEL FOR ROOM-TEMPERATURE MOLTEN-SALTS
FULLER, J
CARLIN, RT
DELONG, HC
HAWORTH, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) : 299 - 300
[5] Room temperature ionic liquids as novel media for 'clean' liquid-liquid extraction
Huddleston, JG
Willauer, HD
Swatloski, RP
Visser, AE
Rogers, RD
[J]. CHEMICAL COMMUNICATIONS, 1998, (16) : 1765 - 1766
[6] Kielbasinski P, 2000, NATO SCI PRT 1 DISAR, V33, P161
[7] Lipase-promoted kinetic resolution of racemic, P-chiral hydroxymethylphosphonates and phosphinates
Kielbasinski, P
Omelanczuk, J
Mikolajczyk, M
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (18) : 3283 - 3287
[8] Biocatalysis in ionic liquids: Markedly enhanced enantioselectivity of lipase
Kim, KW
Song, B
Choi, MY
Kim, MJ
[J]. ORGANIC LETTERS, 2001, 3 (10) : 1507 - 1509
[9] Lipase-catalyzed reactions in ionic liquids
Lau, RM
van Rantwijk, F
Seddon, KR
Sheldon, RA
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4189 - 4191
[10] Stereoselective synthesis of racemic and optically active E-vinyl and E-dienyl sulfoxides via Wittig reaction of α-sulfinyl phosphonium ylides
Mikolajczyk, M
Perlikowska, W
Omelanczuk, J
Cristau, HJ
Perraud-Darcy, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) : 9716 - 9722

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