Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers.: 31P NMR analysis of the enantiomeric composition of oxiranes

被引：11

作者：

Bredikhin, AA ^{[1
]}

Strunskaya, EI ^{[1
]}

Novikova, VG ^{[1
]}

Azancheev, NM ^{[1
]}

Sharafutdinova, DR ^{[1
]}

Bredikhina, ZA ^{[1
]}

机构：

[1] Russian Acad Sci, Kazan Res Ctr, AE Arbuzov Organ & Phys Chem Inst, Kazan 420088, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2004年 / 53卷 / 01期

基金：

俄罗斯基础研究基金会;

关键词：

enantioselective hydrolysis; chiral Co(salen)-catalyst; aryl glycidyl ethers; enantiomeric purity; P-31; NMR; 3-aryloxypropane-1,2-diols; toliprolol; moprolol;

D O I：

10.1023/B:RUCB.0000024851.29744.21

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by P-31 NMR using optically active substituted 2-chloro-1,3,2-dioxaphospholanes. A synthesis of beta-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2-diols was proposed.

引用

页码：213 / 218

页数：6

共 15 条

[1] Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes
A. A. Bredikhin
E. I. Strunskaya
V. G. Novikova
N. M. Azancheev
D. R. Sharafutdinova
Z. A. Bredikhina
Russian Chemical Bulletin, 2004, 53 : 213 - 218
[2] Regiochemistry of cleavage of monosubstituted oxiranes by phosphorochloridites.: Enantiomeric composition of oxiranes by 31P NMR spectral data
Bredikhina, ZA
Novikova, VG
Azancheev, NM
Bredikhin, AA
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2002, 72 (08) : 1207 - 1214
[3] Regiochemistry of Cleavage of Monosubstituted Oxiranes by Phosphorochloridites. Enantiomeric Composition of Oxiranes by 31P NMR Spectral Data
Z. A. Bredikhina
V. G. Novikova
N. M. Azancheev
A. A. Bredikhin
Russian Journal of General Chemistry, 2002, 72 : 1207 - 1214
[4] New chiral organophosphorus derivatizing agent for the determination of enantiomeric composition of chloro- and bromohydrins by 31P NMR spectroscopy
Reymond, S
Brunel, JM
Buono, G
TETRAHEDRON-ASYMMETRY, 2000, 11 (06) : 1273 - 1278
[5] Determination of arylglycerol-β-aryl ethers and other linkages in lignins using DFRC/31P NMR (vol 49, pg 536, 2001)
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Argyropoulos, DS
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (02) : 1068 - 1068
[6] Phospholipid composition analysis of krill oil through HPLC with ELSD: Development, validation, and comparison with 31P NMR spectroscopy
Yu, Hyo-Yeon
Park, Se-Eun
Chun, Hyang Sook
Rho, Jung-Rae
Ahn, Sangdoo
JOURNAL OF FOOD COMPOSITION AND ANALYSIS, 2022, 107
[7] Cyclic phosphorochloridites (chloridates) based on chiral butane-2,3-diol and dihydrobenzoin as reagents for the analysis of enantiomeric compositions of alcohols by 31P NMR spectroscopy
Bredikhin, AA
Bredikhina, ZA
Gaisina, LM
Strunskaya, EI
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RUSSIAN CHEMICAL BULLETIN, 2000, 49 (02) : 310 - 313
[8] 31P NMR determination of the enantiomeric composition of N-phthaloyl-1-aminoalkylphosphonate monoesters using 1-(1-naphthyl)ethylamine and ephedrine as the chiral agents
Glowacki, Z
Hoffmann, M
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 134 : 279 - 285
[9] Analysis of the lipid composition of human and boar spermatozoa by MALDI-TOF mass spectrometry, thin layer chromatography and 31P NMR spectroscopy
Lessig, J
Gey, C
Süss, R
Schiller, J
Glander, HJ
Arnhold, J
COMPARATIVE BIOCHEMISTRY AND PHYSIOLOGY B-BIOCHEMISTRY & MOLECULAR BIOLOGY, 2004, 137 (02): : 265 - 277
[10] Application of 31P NMR spectroscopy in food analysis.: 1.: Quantitative determination of the mono- and diglyceride composition of olive oils
Spyros, A
Dais, P
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (03) : 802 - 805

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