Chiral NMR shift reagents: Mixtures of lanthanide tris (β-diketonates) with chiral carboxylate anions

Magnetic Resonance in Chemistry

Volumn 35, Issue 6, 1997, Pages 395-402

  Wenzel, Thomas J ^a   Bean, Amy C ^a   Dunham, Sarah L ^a  

^a BATES COLLEGE   (United States)

Author keywords

1H NMR; Chiral solvating agent; Enantiomers; Lanthanide; NMR; Optical purity; Shift reagent

Indexed keywords

AMINES; AMINO ACIDS; CARBOXYLATION; CHLORINE COMPOUNDS; ENANTIOMERS; ESTERS; IONS; SUBSTRATES;

1H NMR; ANIONIC SPECIES; CHIRAL SOLVATING AGENTS; DIKETONATE COMPLEXES; ENANTIOMERIC RESOLUTION; ION PAIRS; OPTICAL PURITY; RESOLVING AGENTS; SHIFT REAGENTS; SPECTRA'S;

RARE EARTH ELEMENTS;

EID: 0001682535     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-458x(199706)35:6<395::aid-omr80>3.3.co;2-v     Document Type: Article

References (33)

1. W. H. Pirkle and T. C. Pochapsky, Chem. Rev. 89, 347 (1989).
2. D. D. MacNicol and D. S. Rycroft, Tetrahedron Lett. 2173 (1977).
3. M. Deshmukh, E. Dunach, S. Juge and H. B. Kagan, Tetrahedran Lett. 25, 3467 (1984).
4. E. Dunach and H. B. Kagan, Tetrahedron Lett. 26, 2649 (1985).
5. W. H. Pirkle and A. Tsipouras, Tetrahedron Lett. 26, 2989 (1985).
6. D. Greatbanks and R. Pickford, Magn. Reson. Chem. 25, 208 (1987).
7. A. F. Casy and A. D. Mercer, Magn. Reson. Chem. 26, 765 (1988).
8. S. E. Brown, J. H. Coates, S. F. Lincoln, D. R. Coghlan and C. J. Easton, J. Chem. Soc., Faraday Trans. 87, 2699 (1991).
9. E. Yashima, M. Yamada and Y. Okamato, Chem. Lett. 579 (1994).
10. W. H. Pirkle and Y. Liu, J. Org. Chem. 59, 6911 (1994).
11. W. H. Pirkle and D. L. Sikkenga, J. Org. Chem. 40, 3430 (1975).
12. W. H. Pirkle, D. L Sikkenga and M. S. Pavlin, J. Org. Chem. 42, 384 (1977).
13. T. J. Wenzel, C. A. Morin and A. A. Brechting, J. Org. Chem. 57, 3594 (1992).
14. T. J. Wenzel, R. D. Miles and S. E. Weinstein, Chirality, in press.
15. T. J. Wenzel, M. S. Bogyo and E. L. Lebeau, J. Am. Chem. Soc. 116, 4858 (1994).
16. C. S. Springer, Jr, D. W. Meek and R. E. Sievers, Inorg. Chem. 6, 1105 (1967).
17. N. Oi and H. Kitahara, J. Liq. Chromatogr. 9, 511 (1986).
18. T. J. Wenzel, NMR Shift Reagents, pp. 55-56. CRC Press, Boca Raton, FL (1987).
19. M. J. Bennett, F. A. Cotton, P. Legzdins and S. J. Lippard, Inorg. Chem. 7, 1770 (1968).
20. T. J. Wenzel, T. C. Bettes, J. E. Sadlowski and R. E. Sievers, J. Am. Chem. Soc. 102, 5903 (1980).
21. T. J. Wenzel and R. E. Sievers, Anal. Chem. 53, 393 (1981).
22. T. J. Wenzel and R. E. Sievers, J. Am. Chem. Soc. 104, 382 (1982).
23. T. J. Wenzel and R. E. Sievers, Anal. Chem. 54, 1602 (1982).
24. T. J. Wenzel, A. C. Ruggles and D. R. Lalonde, Jr, Magn. Reson. Chem. 23, 778 (1985).
25. T. J. Wenzel and J. Zaia, J. Org. Chem. 50, 1322 (1985).
26. T. J. Wenzel and J. Zaia, Anal. Chem. 59, 562 (1987).
27. H. Tsukube, H. Shiba and J. Uenishi, J. Chem. Soc., Dalton Trans. 181 (1995).
28. H. M. McConnell and R. E. Robertson, J. Chem. Phys. 29, 1361 (1958).
29. R. M. Silverstein, G. C. Bassler and T. C. Morrill, Spectrometric Identification of Organic Compounds, 5th ed., p. 186. Wiley, New York (1991).
30. N. Oi and H. Kitahara, J. Chromatogr. 265, 117 (1983).
31. Z. W. Wolkowski, C. Beaute and R. Jantzen, J. Chem. Soc., Chem. Commun. 619 (1972).
32. W. H. Pirkle and C. J. Welch, J. Org. Chem. 49, 138 (1984).
33. W. H. Pirkle, C. J. Welch and M. H. Hyun, J. Org. Chem. 48, 5022 (1983).