Resolution of enantiomer signals by diamagnetic lanthanum(III)-N,N,N',N'-tetrakis (2-pyridinylmethyl)-(R)-propylenediamine complex in 1H NMR

Enantiomer

Volumn 4, Issue 2, 1999, Pages 147-150

  Sato, Junjiro ^a   Jin, Hai Ying ^a   Omata, Kenji ^a   Kabuto, Kuninobu ^a   Sasaki, Yoichi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Diamagnetic chiral shift reagent; Lanthanum complex

Indexed keywords

ALPHA AMINO ACID; LANTHANIDE; LANTHANUM; PROPYLENE;

ARTICLE; CHEMICAL STRUCTURE; ENANTIOMER; PH; PRIORITY JOURNAL;

EID: 0032821574     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (13)

1. T.J. Wenzel, NMR Shift Reagent, CRC Press, Boca Raton, FL, 1987.
2. R. Hazama, K. Umakoshi, C. Kabuto, K. Kabuto and Y. Sasaki, J. Chem. Soc., Chem. Commun., 1996, 15-16.
3. Lu(III)-(R)-tppn caused intense broadening toward alanine.
4. 1H NMR spectra were determined under the conditions described in Table I.
5. 3) of La-tpen (tpen = N,N,N′,N′-terakis(2-pyridinylmethyl)ethylenediamine analogous to 1 was reported to be 3.9 at pH 7.2. M. Yashiro, A. Ishikubo, T. Takarada and M. Komiyama, Chem. Lett., 1995, 665-666.
6. Asymmetric disposition of four pyridine rings has been seen in the X-ray structures of a Eu-tppn [2] and Sm-tpen complex. H.-Y. Jin, M. Akiba, K. Umakoshi, Y. Sasaki and K. Kabuto, Acta. Crystallogr., Sect. C 53, 1997, 60-63; Similar structures have been observed on a series of Ln-tppn or Ln-tpen (Ln = Ce, Pr, Nd, Gd, Dy, Er and Yb).
7. H.-Y. Jin, Doctral Dissertation, Hokkaido University, Sapporo, Japan, 1998.
8. L.M. Jackman and S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, International Series of Monographs in Organic Chemistry, Vol. 5, Pergamon: Oxford, UK, 1969, pp. 94-98.
9. 2O.
10. K. Kabuto and Y. Sasaki, J. Chem. Soc., Chem. Commun., 1987, 670-671.
11. (a) D.J. Raber, in T.C. Morril (Ed.), Lanthanide Shift Reagents in Stereochemical Analysis, Methods in Stereochemical Analysis, Vol. 5, VCH, New York, 1986, pp. 55-105.
12. (b) R. Hulst, N. Koen de Vries and B.L. Feringa, J. Org. Chem., 1994, 59, 7453-7458.
13. R.E. Lenkinski and J. Reuben, J. Magn. Res., 1976, 21, 47.