Remarkable amplification of the self-disproportionation of enantiomers on achiral-phase chromatography columns

Angewandte Chemie - International Edition

Volumn 45, Issue 5, 2006, Pages 766-769

  Soloshonok, Vadim A ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Asymmetric synthesis; Chiral resolution; Chirality; Disproportionation; Liquid chromatography

Indexed keywords

AMPLIFICATION; COLUMN CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; PHASE TRANSITIONS; STEREOCHEMISTRY;

ASYMMETRIC SYNTHESIS; CHIRAL COMPOUNDS; CHIRAL RESOLUTION; CHIRALITY; DISPROPORTIONATION;

STOICHIOMETRY;

EID: 31444451709     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503373     Document Type: Article

References (45)

1. a) T. Williams, R. G. Pitcher, P. Bommer, J. Gutzwiller, M. Uskokovic, J. Am. Chem. Soc. 1969, 91, 1871;
2. for other NMR studies, see: b) A. Dobashi, N. Saito, Y. Motoyama, S. Hara, J. Am. Chem. Soc. 1986, 108, 307;
3. c) B. S. Jursic, S. I. Goldberg, J. Org. Chem. 1992, 57, 7172.
4. a) A. Horeau, Tetrahedron Lett. 1969, 3121;
5. b) A. Horeau, J. P. Guette, Tetrahedron 1974, 30, 1923.
6. J. Georges, Spectrochim. Acta A 1995, 51, 985.
7. a) C. Puchot, O. Samuel, E. Dunach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc. 1986, 108, 2353;
8. b) M. Kitamura, S. Suga, M. Niwa, R. Noyori, Z.-X. Zhai, H. Suga, J. Phys. Chem. 1994, 98, 12776;
9. c) M. Kitamura, S. Suga, H. Oka, R. Noyori, J. Am. Chem. Soc. 1998, 120, 9800;
10. d) C. Girard, H. B. Kagan, Can. J. Chem. 2000, 78, 816.
11. Besides the potential practical application of this phenomenon in the development of conceptually new separation techniques, it could lead to models for amplification of the optical activity of chiral compounds under prebiotic conditions, a) S. Bondy, M. Harrington, Science 1979, 203, 1243;
12. b) J. B. Youatt, R. D. Brown, Science 1981, 212, 1145.
13. K. C. Cundy, P. A. Crooks, J. Chromatogr. 1983, 281, 17.
14. a) R. Charles, E. Gil-Av, J. Chromatogr. 1984, 298, 516;
15. b) T.-L. Tsai, K. Herman, E. Hug, B. Rohde, A. S. Dreiding, Helv. Chim. Acta 1985, 68, 2238;
16. c) A. Dobashi, Y. Motoyama, K. Kinoshita, S. Hara, N. Fukasaku, Anal. Chem. 1987, 59, 2209;
17. d) R. Matusch, C. Coors, Angew. Chem. 1989, 101, 624;
18. Angew. Chem. Int. Ed. Engl. 1989, 28, 626;
19. e) E. Loza, D. Lola, A. Kemme, J. Freimanis, J. Chromatogr. A 1995, 708, 231;
20. f) R.-M. Nicoud, J.-N. Jaubert, I. Rupprecht, J. Kinkel, Chirality 1996, 8, 234;
21. g) K. Monde, N. Harada, M. Takasugi, P. Kutschy, M. Suchy, M. Dzurilla, J. Nat. Prod. 2000, 63, 1312;
22. h) M. Suchy, P. Kutschy, K. Monde, H. Goto, N. Harada, M. Takasugi, M. Dzurilla, E. Balentova, J. Org. Chem. 2001, 66, 3940.
23. H. Kosugi, M. Abe, R. Hatsuda, H. Uda, M. Kato, Chem. Commun. 1997, 1857.
24. P. Diter, S. Taudien, O. Samuel, H. B. Kagan, J. Org. Chem. 1994, 59, 370.
25. a) H. Takahata, Yuki Gosei Kagaku Kyokaishi 1996, 54, 708;
26. b) K. Tanaka, H. Osuga, H. Suzuki, Y. Shogase, Y. J. Kitahara, J. Chem. Soc. Perkin Trans. 1 1998, 935;
27. c) B. V. Ernholt, I. B. Thomsen, A. Lohse, I. W. Plesner, K. B. Jensen, R. G. Hazell, X. Liang, A. Jacobsen, M. Bols, Chem. Eur. J. 2000, 6, 278.
28. For instance, in the most recent book (a) and review article (b) on unconventional methods for the resolution of enantiomers, this phenomenon was not even mentioned; a) F. Toda, Enantiomer Separation, Springer, Berlin, 2004;
29. b) E. Fogassy, M. Nogradi, E. Palovics, J. Schindler, Synthesis 2005,1555.
30. [8]
31. a) T. Ono, V. P. Kukhar', V. A. Soloshonok, J. Org. Chem. 1996, 61, 6563;
32. b) V. A. Soloshonok, T. Ono. J. Org. Chem. 1997, 62, 3030;
33. c) V. A. Soloshonok, T. Ono, I. V. Soloshonok, J. Org. Chem. 1997, 62, 7538;
34. d) V. A. Soloshonok, I.V. Soloshonok, V. P. Kukhar', V. K. Svedas, J. Org. Chem. 1998, 63, 1878;
35. for recent publications, see: e) V. A. Soloshonok, H. Ohkura, K. Uneyama, Tetrahedron Lett. 2002, 43, 5449;
36. f) H. Ohkura, D. O. Berbasov, V. A. Soloshonok, Tetrahedron Lett. 2003, 44, 2417;
37. g) V. A. Soloshonok, D. O. Berbasov, J. Fluorine Chem. 2004, 125, 1757.
38. All experiments were conducted under the same conditions unless otherwise stated. Silica gel (200-300 mesh) was purchased from Natland International Corporation. Temperature: ambient (T = 21-23°C); amount of sample: m = 0.0300 ± 0.0001 g; columns: diameter d = 16 mm, length l = 230 mm; amount of each fraction V = 7 mL. The enantiomeric excess was determined by HPLC analysis: Sumichiral OA-4500, l = 25 cm, d = 4.6 mm.
39. [10c]
40. a) V. A. Soloshonok, V. P. Kukhar', S. V. Galushko, N. Y. Svistunova, D. V. Avilov, N. A. Kuzmina, N. I. Raevski, Y. T. Struchkov, A. P. Pisarevsky, Y. N. Belokon, J. Chem. Soc. Perkin Trans. 1 1993, 3143;
41. b) V. A. Soloshonok, A. D. Kacharov, D. V. Avilov, T. Hayashi, Tetrahedron Lett. 1996, 37, 7845;
42. c) P. Bravo, A. Farina, V. P. Kukhar', A. L. Markovsky, S. V. Meille, V. A. Soloshonok, A. E. Sorochinsky, F. Viani, M. Zanda, C. Zappala, J. Org. Chem. 1997, 62, 3424;
43. d) V. A. Soloshonok, A. D. Kacharov, D. V. Avilov, K. Ishikawa, N. Nagashima, T. Hayashi, J. Org. Chem. 1997, 62, 3470;
44. e) V. A. Soloshonok, D. V. Avilov, V. P. Kukhar', L. V. Meervelt, N. Mischenko, Tetrahedron Lett. 1997, 38, 4671.
45. 2 stationary phase, hexane/dichloromethane as eluent).