CYCLODEXTRIN DERIVATIVES AS CHIRAL SELECTORS - INVESTIGATION OF THE INTERACTION WITH (R,S)-METHYL-2-CHLOROPROPIONATE BY ENANTIOSELECTIVE GAS-CHROMATOGRAPHY, NMR-SPECTROSCOPY, AND MOLECULAR-DYNAMICS SIMULATION

被引:66
作者
KOHLER, JEH [1 ]
HOHLA, M [1 ]
RICHTERS, M [1 ]
KONIG, WA [1 ]
机构
[1] CONSORTIUM ELEKROCHEM IND,W-8000 MUNICH 70,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1992年 / 31卷 / 03期
关键词
D O I
10.1002/anie.199203191
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The greater stability of the complex of methyl (S)-2-chloropropionate ((S)-1) and the hydrophobic cyclodextrin derivative 2, is deduced from its characterization by gas chromatography and NMR spectroscopy as well as from molecular dynamics simulations of the (R,S)-1/2, (R)-1/2, and (S)-1/2 systems: on complexation the H-1 NMR signals of the (S) enantiomer undergo a downfield shift of up to DELTA-delta = 0.5 relative to those of the (R) enantiomer. Thus, cyclodextrins can be used not only for enantiomeric separations, but also as chiral shift reagents. R2 = R6 = n-pentyl, R3 = acetyl.
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页码:319 / 320
页数:2
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