Enantiodiffertiation of aryl-substituted heterocycles: A mechanistic study using γ-lactones

Journal of Chromatography A

Volumn 775, Issue 1-2, 1997, Pages 81-90

  Pirkle, William H ^a   Spence, Patrick L ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Lactones; Chiral recognition; Chiral stationary phases, LC

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; LACTONE; TETRAHYDRO 2 FURANONE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHROMATOGRAPHY; COMPLEX FORMATION; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030844579     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9673(97)00204-5     Document Type: Article

References (42)

1. Francotte E., Lohmann D. Helv. Chim. Acta. 70:1987;1569.
2. Francotte E., Wolf R.M. Chirality. 2:1990;16.
3. Hünig S., Klaunzer N., Günther K. J. Chromatogr. 481:1989;387.
4. Armstrong D.W., Stalcup A.M., Hilton M.L., Duncan J.D., Faulkner J.R., Chang S. Anal. Chem. 62:1990;1610.
5. Lienne M., Caude M., Rosset R., Tambute A. J. Chromatogr. 448:1988;55.
6. Kaida Y., Okamoto Y. J. Chromatogr. 641:1993;267.
7. Maier N., Uray G. J. Chromatogr. A. 740:1996;11.
8. Pirkle W.H., Welch C.J. J. Liq. Chromatogr. 15:1992;1947.
9. Pirkle W.H., Welch C.J., Lamm B. J. Org. Chem. 57:1992;3854.
10. Pirkle W.H., Welch C.J., Wilson S.R. Chirality. 6:1994;615.
11. Pirkle W.H., Selness S.R. J. Org. Chem. 60:1995;3252.
12. Pirkle W.H., Welch C.J. J. Chromatogr. A. 683:1994;347.
13. Pirkle W.H., Koscho M.E., Wu Z. J. Chromatogr. A. 726:1996;91.
14. Pirkle W.H., Brice L.J., Caccamese S., Principato G., Failla S. J. Chromatogr. A. 721:1996;241.
15. B. Rothstein, Bull. Chim. Soc. Fr. (1935) 80.
16. Sato M., Kosasayama A., Uchimaru F. Chem. Pharm. Bull. 29:1981;2885.
17. M. Julia, S. Julia and B. Bémont, Bull. Chim. Soc. Fr. (1960) 304.
18. I.W. Lawston and T.D. Inch, J. Chem. Soc. Perkins Trans. I (1983) 2629.
19. M.A. Rizzacasa and M.V. Sargent, J. Chem. Soc. Perkins Trans. I (1991) 845.
20. T. Mandai, S. Hasegawa, T. Fujimoto, M. Kawada, J. Nokami and J. Tsuji, Synlett. (1990) 85.
21. Arcadi A., Bernocchi E., Cacchi S., Marinolli F. Tetrahedron. 47:1991;1525.
22. Helmchen G., Nill G. Angew. Chem. Int. Ed. Eng. 18:1979;65.
23. McGahey L. J. Chem. Ed. 63:1986;1101.
24. Masuya K., Tanino K., Kuwajima I. Tetrahedron Lett. 35:1994;7965.
25. Cohen N., Banner B., Blount J., Tsai M., Saucy G. J. Org. Chem. 38:1973;3229.
26. Berger F. Liebigs Ann. Chem. 482:1930;55.
27. P. Bavin, D. Hansell and R. Spickett, J. Chem. Soc. (1964) 4535.
28. Gutman A.L., Zuobi K., Bravdo T. J. Org. Chem. 55:1990;3546.
29. Pirkle W.H., Sowin T.J. J. Org. Chem. 52:1987;3011.
30. Scheibye S., Kristensen J., Lawesson S.O. Tetrahedron. 35:1979;1339.
31. P. Rioult and J. Vialle, Bull. Chim. Soc. Fr. (1965) 3312.
32. Letsinger R.L., Pollart D.F. J. Am. Chem. Soc. 78:1956;6079.
33. A. Pernot and A. Willemart, Bull. Chim. Soc. Fr. (1953) 321.
34. M. Fieser and L. Fieser, Reagents for Organic Synthesis, Wiley-Interscience, New York, Vol. 1, 1988, p. 584.
35. Tanaka J., Miyake T., Iwasaki N., Adachi K. Bull. Chem. Soc. Jpn. 65:1992;2851.
36. Meyers A., Temple D., Haidukewych D., Miihelich E.D. J. Org. Chem. 39:1974;2787.
37. Fristad W.E., Peterson J.R. J. Org. Chem. 50:1985;10.
38. Giordano C., Belli A., Cassagrande F., Guglielmetti G., Citterio A. J. Org. Chem. 46:1981;3149.
39. A. Albinati, P. Bravo, F. Ganazzoli, G. Resnati and F. Viani, J. Chem. Soc. Perkins Trans. I (1986) 1405.
40. Takahashi H., Hattori K., Higashiyama K., Ueno Y. Chem. Pharm. Bull. 38:1990;1062.
41. M.J. Janssen, in A. Senning (Editor), Topics in Sulfur Chemistry, Georg Thieme Publishers, Stuttgart, Vol. 4, 1979, p. 225.
42. Ozawa F., Kubo A., Hayashi T. J. Am. Chem. Soc. 113:1991;1417.