Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases

Journal of Chromatography A

Volumn 1357, Issue , 2014, Pages 172-181

  Woods, Ross M ^a   Patel, Darshan C ^a   Lim, Yeeun ^a   Breitbach, Zachary S ^a   Gao, Hongyin ^c   Keene, Craig ^c   Li, Gongqiang ^c   Kürti, László ^c   Armstrong, Daniel W ^a,b  

^a UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^b AZYP LLC   (United States)

^c UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

Atropisomers; Biaryls; Chiral HPLC; Cyclofructans; Preparative HPLC

Indexed keywords

ENANTIOMERS;

ATROPISOMERS; BIARYLS; CHIRAL HPLC; CYCLOFRUCTANS; PREPARATIVE HPLC;

SEPARATION;

1 (2 AMINO 3 BROMO 4 METHYLPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3 BROMOPHENYL) 6 METHOXYNAPHTHALEN 2 OL; 1 (2 AMINO 3 BROMOPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3 CHLORO 4 METHYLPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3 CHLORO 5 METHYLPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3 CHLORO 6 FLUOROPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3 CHLORO 6 METHYLPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3 CHLOROPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3,4,5 TRICHLOROPHENYL) 6 METHOXYNAPHTHALEN 2 OL; 1 (2 AMINO 3,4,5 TRICHLOROPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3,5 DICHLORO 4 METHYLPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3,5 DICHLOROPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3,6 DIBROMOPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINO 3,6 DICHLOROPHENYL)NAPHTHALEN 2 OL; 1 (2 AMINOPHENYL)NAPHTHALEN 2 AMINE; 2' AMINO 3' BROMO 6' METHOXY [1,1' BIPHENYL] 2 OL; 2' AMINO [1,1' BINAPHTHALEN] 2 OL; 3,3' BIS(3,5 DIMETHYLPHENYL) 5,5',6,6',7,7',8,8' OCTAHYDRO [1,1' BINAPHTHALENE] 2,2' DIOL; 3,3' DIBROMO 5,5',6,6',7,7',8,8' OCTAHYDRO [1,1' BINAPHTHALENE] 2,2' DIOL; 3,3' DIPHENYL [1,1' BINAPHTHALENE] 2,2' DIAMINE; 3,3' DIPHENYL [2,2' BINAPHTHALENE] 1,1' DIOL; 5,5' DIMETHOXY [1,1' BINAPHTHALENE] 2,2' DIAMINE; 6,6' DIBROMO [1,1' BINAPHTHALENE] 2,2' DIOL; 7,7' DIMETHOXY [1,1' BINAPHTHALENE] 2,2' DIAMINE; CYCLOFRUCTAN; FRUCTAN; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG; [1,1' BINAPHTHALENE] 2,2' DIAMINE; [1,1' BINAPHTHALENE] 2,2' DIOL;

ADSORPTION KINETICS; ANALYTICAL PARAMETERS; ARTICLE; BIARYL ATROPISOMER; CHEMICAL MODIFICATION; CHIRAL CHROMATOGRAPHY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PRIORITY JOURNAL; SEPARATION TECHNIQUE; TEMPERATURE SENSITIVITY; THERMODYNAMICS; VAN T HOFF PLOT;

ATROPISOMERS; BIARYLS; CHIRAL HPLC; CYCLOFRUCTANS; PREPARATIVE HPLC;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUCTANS; ORGANIC CHEMICALS; STEREOISOMERISM; THERMODYNAMICS;

EID: 84905049087     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2014.04.080     Document Type: Article

References (35)

1. Pu L. Chem. Rev. 1998, 98:2405.
2. Ding K.L., Li X., Ji B.M., Guo H.C., Kitamura M. Curr. Org. Synth. 2005, 2:499.
3. Guillena G., Hita M.D., Najera C., Viozquez S.F. J. Org. Chem. 2008, 73:5933.
4. Aleman J., Cabrera S. Chem. Soc. Rev. 2013, 42:774.
5. Liao J., Sun X., Cui X., Yu K., Zhu J., Deng J. Chem. Eur. J. 2003, 9:2611.
6. Patchett A.A., Nargund R.P. Annual Reports in Medicinal Chemistry 2000, 289. Academic Press, Waltham, MA.
7. Horton D.A., Bourne G.T., Smythe M.L. Chem. Rev. 2003, 103:893.
8. Li G.Q., Gao H., Keene C., Devonas M., Ess D.H., Kurti L. J. Am. Chem. Soc. 2013, 135:7414.
9. Gao H.Y., Ess D.H., Yousufuddin M., Kurti L. J. Am. Chem. Soc. 2013, 135:7086.
10. Bringmann G., Gulder T., Gulder T.A.M., Breuning M. Chem. Rev. 2010, 111:563.
11. Gubitz G. Chromatographia 1990, 30:555.
12. Christodoulou E.A. Curr. Org. Chem. 2010, 14:2337.
13. Qiu H., Padivitage N.L.T., Frink L.A., Armstrong D.W. Tetrahedron: Asymmetry 2013, 24:1134.
14. Huang K., Breitbach Z.S., Armstrong D.W. Tetrahedron: Asymmetry 2006, 17:2821.
15. Armstrong D.W., He L., Yu T., Lee J.T., Liu Y.-S. Tetrahedron: Asymmetry 1999, 10:37.
16. Armstrong D.W., Lee J.T., Chang L.W. Tetrahedron: Asymmetry 1998, 9:2043.
17. Nelson T.D., Welch C.J., Rosen J.D., Smitrovich J.H., Huffman M.A., McNamara J.M., Mathre D.J. Chirality 2004, 16:609.
18. Lipka E., Yous S., Furman C., Carato P., Deghaye C., Bonte J.P., Vaccher C. Chromatographia 2012, 75:337.
19. Roussel C., Suteu C. Enantiomer 1997, 2:449.
20. Hyun M.H., Lee G.S., Han S.C. Bull. Korean Chem. Soc. 1999, 20:1245.
21. Loukotkova L., Rambouskova M., Bosakova Z., Tesarova E. Chirality 2008, 20:900.
22. Prikle W.H., Welch C.J., Zych A.J. J. Chromatogr. 1993, 648:101.
23. Armstrong D.W., Ward T.J., Czech A., Czech B.P., Bartsch R.A. J. Org. Chem. 1985, 50:5556.
24. Iuliano A., Pieroni E., Salvadori P. J. Chromatogr. A 1997, 786:355.
25. Zaruba K., Kral V. Tetrahedron: Asymmetry 2002, 13:2567.
26. Kalíková K., Janečková L., Armstrong D.W., Tesařová E. J. Chromatogr. A 2011, 1218:1393.
27. Smuts J.P., Hao X.-Q., Han Z., Parpia C., Krische M.J., Armstrong D.W. Anal. Chem. 2013, 86:1282.
28. Weng W., Guo H.X., Zhan F.P., Fang H.L., Wang Q.X., Yao B.X., Li S.X. J. Chromatogr. A 2008, 1210:178.
29. Sun P., Wang C., Breitbach Z.S., Zhang Y., Armstrong D.W. Anal. Chem. 2009, 81:10215.
30. Sun P., Armstrong D.W. J. Chromatogr. A 2010, 1217:4904.
31. Sun P., Wang C.L., Padivitage N.L.T., Nanayakkara Y.S., Perera S., Qiu H.X., Zhang Y., Armstrong D.W. Analyst 2011, 136:787.
32. Gondová T., Petrovaj J., Kutschy P., Armstrong D.W. J. Chromatogr. A 2013, 1272:100.
33. Janečková L., Kalíková K., Vozka J., Armstrong D.W., Bosáková Z., Tesařová E. J. Sep. Sci. 2011, 34:2639.
34. Padivitage N.L.T., Dodbiba E., Breitbach Z.S., Armstrong D.W. Drug Test. Anal. 2013, 10.1002/dta.1534.
35. Perera S., Na Y.-C., Doundoulakis T., Ngo V.J., Feng Q., Breitbach Z.S., Lovely C.J., Armstrong D.W. Chirality 2013, 25:133.