Samarium(III)-propylenediaminetetraacetate complex: A water-soluble chiral shift reagent for use in high-field NMR

Organic Letters

Volumn 2, Issue 23, 2000, Pages 3543-3545

  Inamoto, Atsushi ^a   Ogasawara, Koji ^a   Omata, Kenji ^a   Kabuto, Kuninobu ^a   Sasaki, Yoichi ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000997785     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006379b     Document Type: Article

References (22)

1. (a) Wenzel, T. J. NMR Shift Reagents; CRC Press: Boca Raton, Florida 1987.
2. (b) Frazer, R. R. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Chapter 9, pp 173-196.
3. (c) Sullivan, G. R. In Topics in Stereochemistry; Eliel, E. L., Allinger, N. L., Eds.; Wiley & Sons: New York, 1978; pp 287-329.
4. Yeh, H. J. C; Balani, S. K.; Yagi, H. J.; Green, R. M. E.; Sharma, N. D.; Boyd, D. R.; Jerina, D. M. J. Org. Chem. 1986, 51, 5439-5443.
5. (a) Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1987, 670-671.
6. (b) Kabuto, K.; Sasaki, Y. Chem. Lett. 1989, 385-388.
7. (c) Kabuto, K.; Sasaki, Y. Tetrahedron Lett. 1990, 31, 1031-1034.
8. (d) Kabuto, K.; Sasaki, K.; Sasaki, Y. Tetrahedron: Asymmetry 1992, 3, 1357-1360.
9. Horrocks, W. DeW., Jr.; Sipe, J. P., III. J. Am. Chem. Soc. 1971, 93, 6800-6804.
10. Sweeting, L. M.; Crans, D. C.; Whitesides, G. M J. Org. Chem. 1987, 52, 2273-2276.
11. An attempt to solve this problem by use of a diamagnetic lanthanum complex has been reported: Sato, J.; Jin, H.-Y.; Omata, K.; Kabuto, K.; Sasaki, Y. Enantiomer 1999, 4, 147-150.
12. Ce(III)-pdta showed similar properties. Details will be published elswhere.
13. (a) Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1984, 316-318.
14. (b) Kabuto, C.; Kabuto, K.; Sasaki, Y.; Nishiyama, T.; Umakoshi, K. J. Chem. Soc., Chem. Commun. 1993, 381-383.
15. Serious line broadening was also observed for other water-soluble chiral shift reagents; see: Hulst, R.; Koen de Vries, N.; Feringa, B. L. J. Org. Chem. 1994, 59, 7453-7458. Hazama, R.; Umakoshi, K.; Kabuto, C.; Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1996, 15-16.
16. Serious line broadening was also observed for other water-soluble chiral shift reagents; see: Hulst, R.; Koen de Vries, N.; Feringa, B. L. J. Org. Chem. 1994, 59, 7453-7458. Hazama, R.; Umakoshi, K.; Kabuto, C.; Kabuto, K.; Sasaki, Y. J. Chem. Soc., Chem. Commun. 1996, 15-16.
17. Lenkinski, R. E.; Reuben, J. J. Magn. Reson. 1976, 21, 47-56.
18. Bulsing, J. M.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 1981, 1201-1202.
19. There have been no reports on the practical use of samarium chiral shift reagents, though preparation of a reagent was reported; see: Schurig, V. Tetrahedron Lett. 1972, 13, 3297-3300.
20. Cotton, S. Lanthanides and Actinides; Oxford University Press: New York, 1991; pp 33-34.
21. 2O, [D]/[L]=1/2) in an NMR tube, and NMR spectra were determined.
22. Other proton and carbon signals of the imidazole ring conformed to the rule.