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  • Amino alcohols  (1)
  • Cyclodextrin derivatives  (1)
  • 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
  • Dynamic gas chromatography
  • Cyclodextrins
  • 1995-1999  (3)
Collection
Keywords
Publisher
Years
Year
  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Journal of High Resolution Chromatography 20 (1997), S. 257-260 
    ISSN: 0935-6304
    Keywords: Enantioselective GC ; Diterpene Hydrocarbons ; Cyclodextrin derivatives ; Essential oils ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomeric diterpene hydrocarbons were isolated from different plants and identified by mass spectrometric and NMR investigations. All enantiomeric pairs could be resolved by capillary gas chromatography using either heptakis(2,6-di-O-methyl-3-O-pen-tyl)-β-cyclodextrin or heptakis(6-O-tert-butyldimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin as chiral stationary phases.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0947-3440
    Keywords: Atropisomers ; Biphenyls, axially chiral ; Enantiomerization ; Dynamic gas chromatography ; Polarimetry ; Energy barriers ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: We have synthesized a series of 2,2′-substituted biphenyls and particularly derivatives of 2,2′-bis(trifluoromethyl)biphenyl (4) with either one or two fluoro, chloro, bromo, amino, nitro or methoxy substituents in the para positions for investigating the influence of these substituents on the rotational energy barrier of the biphenyls by polarimetry and dynamic gas chromatography (DGC). Axially chiral biphenyls with at least two bulky substituents in the ortho positions were separated by gas chromatography on selectively modified cyclodextrins. Due to competition between resolution and enantiomerization in the gas chromatographic column 2-tert-butyl-2′-isopropyl- (2), 2-isopropyl-2′-(trifluoromethyl)biphenyl (5), and some para-substituted derivatives of 4 show temperature-dependent interconversion profiles and coalescence phenomena in analogy to dynamic NMR studies. The accelerating effect on the rate of enantiomerization of electron-donating groups in the para positions and the decelerating effect of electron-accepting groups has been determined. Dynamic gas chromatography is shown to be a useful supplement to studies of thermal enantiomerization kinetics of optically enriched or separated compounds by polarimetry for the investigation of energy barriers of atropisomeric biphenyls.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1434-1948
    Keywords: Pyridine N-oxide ; Pyridine ; Asymmetric catalysis ; Amino acids ; Amino alcohols ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting from picolinic acids 3 and 4, the amino acid-derived 2-aminoacylpyridine N-oxides 1a,c-e and 2,6-bis(aminoacyl)pyridine N-oxides 2b-e can be prepared in two steps by the coupling of picolinic acid N-oxides 5 and 6 under Appel conditions with the corresponding L-amino acid ester or (1R,2S)-norephedrine. Compounds 1 and 2 were used as chiral ligands in two different asymmetric catalyses. In the catalytic addition of diethylzinc to benzaldehyde 11, low enantioselectivities (2-29% ee) were obtained regardless of the amino acid moiety. However, the corresponding 2,6-bis(aminoacyl)pyridines 7 and 8 led to increased ee values (55% ee). In the catalytic reduction of ketones 9a-c to alcohols 10a-c low enantioselectivities were observed for alanine-, valine-, and leucine-derived N-oxides 1a,c and 2b,c. An increase of selectivity was observed for bis-methionine ligand 2d (32-38% ee) relative to that of mono-methionine ligand 1d (7-16% ee). However, mono-norephedrine ligand 1e (≤ 64% ee) and the corresponding bis-norephedrine ligand 2e (≤ 51% ee) displayed the highest selectivities. The influence of the N-oxide moiety on the enantioselectivity was demonstrated by the observation that 2,6-bis(aminoacyl)pyridines 7 and 8 gave much lower selectivities than the corresponding pyridine N-oxides 2d and e.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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