A new exciton-coupled circular dichroism method for assigning the absolute configuration in acyclic α- and β-hydroxy carboxylic acids

Tetrahedron Asymmetry

Volumn 8, Issue 1, 1997, Pages 11-14

  Gimple, Olaf ^a   Schreier, Peter ^a   Humpf, Hans Ulrich ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID;

ARTICLE; DRUG STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY; TECHNIQUE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0031037132     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00490-9     Document Type: Article

References (31)

1. (a) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
2. (b) Nakanishi, K.; Berova, N. In Circular Dichroism Principles and Applications; Nakanishi, K.; Berova, N.; Woody, R. W., Eds; VCH Publishers Inc.: New York, NY, 1994.
3. (a) Cai, G.; Bozhkova, N.; Odingo, J.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1993, 115, 7192-7198.
4. (b) Gargiulo, D.; Ikemoto, N.; Odingo, J.; Bozhkova, N.; Iwashita, T.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1994, 116, 3760-3767.
5. Matile, S.; Berova, N.; Nakanishi, N.; Novkova, S.; Philipova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021-7022.
6. (a) Person, R.V.; Monde, K.; Humpf, H.-U.; Berova, N.; Nakanishi, K. Chirality 1995, 7, 128-135.
7. (b) Schreder, B.; Lukacs, Z.; Schmitt, M.; Schreier, P.; Humpf, H.-U. Tetrahedron: Asymmetry 1996, 7, 1543-1546.
8. (a) Prelog, V.; Wilhelm, M.; Bright, D. B. Helv. Chim. Acta 1954, 37, 221-224.
9. (b) Lee, J. B.; Downie, I. M. Tetrahedron 1967, 23, 359-363.
10. (c) Mori, K.; Takigawa, T.; Matsuo, T. Tetrahedron 1979, 35, 933-940.
11. (d) Comprehensive Organic Chemistry; Barton, R. H. D., Ollis, D. W., Eds.; Pergamon Press: Oxford, 1979; 69-106.
12. (a) Wong, C.-H; Matos, J. R. J. Org. Chem. 1985, 50, 1992-1994.
13. (b) Nakamura, K.; Inoue, K.; Ushio, K.; Oka, S.; Ohno, A. J. Org. Chem. 1988, 53, 2589-2593.
14. (c) Effenberger, F. Angew. Chemie 1994, 706, 1609-1619.
15. (d) Adam, W.; Fell, R. T.; Hoch, U.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1995, 6, 1047-1050.
16. (e) Adam, W.; Lazarus, M.; Saha-Möller, C. R.; Schreier, P. Tetrahedron: Asymmetry 1996, 7, 2287-2292.
17. (a) Evans, D. A.; Morrissey, M. M.; Dorow, R. I. J. Am. Chem. Soc. 1985, 107, 4346-4348.
18. (b) Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Org. Chem. 1986, 51, 3394-3396.
19. (c) Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431-3434.
20. (d) Mikami, K.; Terada, M.; Nakai, J. J. Am. Chem. Soc. 1990, 112, 3949-3954.
21. (a) Wiesler, W. T.; Nakanishi, K. J. Am. Chem. Soc. 1989, 111, 3446-3447.
22. (b) Wiesler, W. T.; Nakanishi, K. J. Am. Chem. Soc. 1989, 111, 9205-9213.
23. (c) Wiesler, W. T.; Nakanishi, K. J. Am. Chem. Soc. 1990, 112, 5574-5583.
24. (a) Nakaya, T.; Tomomoto, T.; Imoto, M. Bull. Chem. Soc. Japn. 1967, 40, 691-692.
25. (b) Nimura, N.; Kinoshita, T. Anal. Lett. 1980, 13, 192-202.
26. (c) commercially available from Lancaster, Mühlheim.
27. Humpf, H.-U.; Zhao, N.; Berova, N.; Nakanishi, K.; Schreier, P. J. Nat. Prod. 1994, 57, 1761-1765.
28. 254, 2 mm, E. Merck). Solvent system: diethyl ether, yield 80-90%. The anthrylmethylester (0.025 mmol) was then treated with 2-naphthoyltriazole (0.03 mmol) and a catalytic amount of DBU in acetonitrile (1 mL) at RT for 10 h. The reaction mixture was concentrated and purified by prep TLC as described above (yield 90%). Solvent system: diethyl ether/pentane (1:1).
29. -1.
30. 2), 7.40 (m, 4H, Ar), 7.56 (m, 2H, Ar), 7.81 (m, 6H, Ar), 8.25 (d, J=8.4 Hz, 2H, Ar), 8.33 (s, 1H, Ar), 8.34 (s, 1H, Ar).
31. This conclusions are based on preferred torsion angles for interacting transition dipoles obtained by computer analysis with MacroModel 5.0 using the modified Allinger MM2 force field.