Cinchona alkaloid induced chiral discrimination for the determination of the enantiomeric composition of α-trifluoromethylated-hydroxyl compounds by 19F NMR spectroscopy

被引:29
作者
Abid, M [1 ]
Török, B [1 ]
机构
[1] Michigan Technol Univ, Dept Chem, Houghton, MI 49931 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/j.tetasy.2005.02.034
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The determination of the enantiomeric composition of alpha-trifluoromethylated-hydroxyl compounds using cinchona alkaloids as chiral selectors is described. The interaction between the alkaloid and trifluoromethylated-hydroxyl compounds converted the enantiotopic nuclei to diastereotopic nuclei observed by F-19 NMR spectroscopy. A wide variety of target molecules have been studied to highlight the broad applicability of the method. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1547 / 1555
页数:9
相关论文
共 59 条
[51]  
TOROK M, IN PRESS J BIOL CHEM
[52]   Unexpected addition of methyl 3,3,3-trifluoropyruvate to "push-pull' enamines having a methyl group at α-position [J].
Volochnyuk, DM ;
Kostyuk, AN ;
Sibgatulin, DA ;
Petrenko, AE .
SYNTHESIS-STUTTGART, 2004, (15) :2545-2549
[53]   (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid and its ytterbium(III) complex as chiral NMR discriminating agents [J].
Wenzel, TJ ;
Thurston, JE .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1243-1248
[54]   Chiral recognition in NMR spectroscopy using crown ethers and their ytterbium(III) complexes [J].
Wenzel, TJ ;
Freeman, BE ;
Sek, DC ;
Zopf, JJ ;
Nakamura, T ;
Jin, YZ ;
Hirose, K ;
Tobe, Y .
ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 2004, 378 (06) :1536-1547
[55]   Utility of crown ethers derived from methyl β-D-galactopyranoside and their lanthanide couples as chiral NMR discriminating agents [J].
Wenzel, TJ ;
Thurston, JE ;
Sek, DC ;
Joly, JP .
TETRAHEDRON-ASYMMETRY, 2001, 12 (08) :1125-1130
[56]  
WENZEL TJ, 2000, TREND ORGAN CHEM, V8, P51
[57]   ASYMMETRIC CATALYSIS BY ALKALOIDS [J].
WYNBERG, H .
TOPICS IN STEREOCHEMISTRY, 1986, 16 :87-129
[58]   Catalytic, highly enantioselective Friedel-crafts reactions of aromatic and heteroaromatic compounds to trifluoropyruvate. A simple approach for the formation of optically active aromatic and heteroaromatic hydroxy trifluoromethyl esters [J].
Zhuang, W ;
Gathergood, N ;
Hazell, RG ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :1009-1013
[59]  
ZIEF M, 1988, CHROMATOGRAPHIC CHIR, V40