5-Amino-4-aryl-2,2-dimethyl-1,3-dioxans: application as chiral NMR shift reagents and derivatizing agents for acidic compounds
作者： Dieter Enders , Christian R Thomas , Jan Runsink
DOI: 10.1016/S0957-4166(99)00003-8
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摘要: Abstract The use of (4 S ,5 )-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxan (ADPD) and R )-5-amino-(4′-biphenyl)-2,2-dimethyl-1,3-dioxan (ABDD) as chiral solvating agents (CSA) for the ee determination compounds bearing an acidic proton by means 1 H NMR spectroscopy is demonstrated. In addition, based on well known rigid conformation these amines, ADPD ABDD are suitable derivatizing (CDAs) in order to determine absolute configurations.
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sci-hub.se 参考文章(17)
Barth�l�my Nyasse, Leif Grehn, Ulf Ragnarsson, Hernani L. S. Maia, Luis S. Monteiro, Ivo Leito, Ilmar Koppel, Juta Koppel, Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pK a of sulfonamides Journal of the Chemical Society, Perkin Transactions 1. pp. 2025- 2031 ,(1995) , 10.1039/P19950002025
Barry M. Trost, John L. Belletire, Stephen Godleski, Patrick G. McDougal, James M. Balkovec, John J. Baldwin, Marcia E. Christy, Gerald S. Ponticello, Sandor L. Varga, James P. Springer, On the use of the O-methylmandelate ester for establishment of absolute configuration of secondary alcohols Journal of Organic Chemistry. ,vol. 51, pp. 2370- 2374 ,(1986) , 10.1021/JO00362A036
S.G. Allenmark, John D. Green, Chromatographic Enantioseparation: Methods and Applications ,(1988)
Takenori Kusumi, Ikuko Ohtani, Yoshinobu Inouye, Hiroshi Kakisawa, Absolute configurations of cytotoxic marine cembranolides; Consideration of mosher's method Tetrahedron Letters. ,vol. 29, pp. 4731- 4734 ,(1988) , 10.1016/S0040-4039(00)80593-6
Friedrich Hammerschmidt, Li Yong-Fu, Determination of absolute configuration of α-hydroxyphosphonates by 31P NMR spectroscopy of corresponding mosher esters Tetrahedron. ,vol. 50, pp. 10253- 10264 ,(1994) , 10.1016/S0040-4020(01)81758-0
Ikuko Ohtani, Takenori Kusumi, Yoel Kashman, Hiroshi Kakisawa, High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids Journal of the American Chemical Society. ,vol. 113, pp. 4092- 4096 ,(1991) , 10.1021/JA00011A006
Julius v. Braun, Ernst Anton, Karl Weißbach, Die Methylierung des alkoholischen Hydroxyls vom Standpunkt der Elektronen-Theorie Berichte der deutschen chemischen Gesellschaft (A and B Series). ,vol. 63, pp. 2847- 2861 ,(1930) , 10.1002/CBER.19300631027
James A. Dale, David L. Dull, Harry S. Mosher, .alpha.-Methoxy-.alpha.-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines Journal of Organic Chemistry. ,vol. 34, pp. 2543- 2549 ,(1969) , 10.1021/JO01261A013
R. Gleiter, E. Pretsch, T. Clerc, J. Seibl und W. Simon: Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden. Springer Verlag, Berlin-Heidelberg-New York 1976. 312 S., Preis: DM 28,-. Berichte der Bunsengesellschaft für physikalische Chemie. ,vol. 81, pp. 352- 352 ,(1977) , 10.1002/BBPC.19770810323
Volker Schurig, Hans-Peter Nowotny, Gas Chromatographic Separation of Enantiomers on Cyclodextrin Derivatives Angewandte Chemie. ,vol. 29, pp. 939- 957 ,(1990) , 10.1002/ANIE.199009393