Preparation and evaluation of novel chiral stationary phases covalently bound with chiral pseudo-18-crown-6 ethers

Tetrahedron Letters

Volumn 44, Issue 8, 2003, Pages 1549-1551

  Hirose, Keiji ^a   Nakamura, Takashi ^a   Nishioka, Ryota ^b   Ueshige, Tetsuro ^b   Tobe, Yoshito ^a  

^a OSAKA UNIVERSITY   (Japan)

^b Sumika Chemicals Analysis Service Ltd   (Japan)

Author keywords

Chiral recognition; Chiral stationary phase; Crown ether

Indexed keywords

AMINE; ETHER DERIVATIVE; HYDROXYL GROUP; PSEUDO 18 CROWN 6 ETHER; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHIRALITY; COVALENT BOND; ENANTIOMER; LIPOPHILICITY; SYNTHESIS;

EID: 0037450460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00020-0     Document Type: Article

References (20)

1. Sousa L.R., Sogah G.D.Y., Hofmann D.H., Cram D.J. J. Am. Chem. Soc. 100:1978;4569-4576.
2. Sogah G.D.Y., Cram D.J. J. Am. Chem. Soc. 101:1979;3035-3042.
3. Shinbo T., Yamaguchi T., Nishimura K., Sugiura M. J. Chromatogr. 405:1987;145-153.
4. Shinbo T., Yamaguchi T., Yanagishita H., Kitamono D., Sakaki K., Sugiura M. J. Chromatogr. 625:1992;101-108.
5. Instruction Manual for CROWNPAK CR (1), Daicel Chemical Industries.
6. Hyun M.H., Jin J.S., Lee W. Bull. Korean Chem. Soc. 19:1998;819-821.
7. Machida Y., Nishi H., Nakamura K., Nakai H., Sato T. J. Chromatogr. A. 805:1998;85-92.
8. Hyun M.H., Jin J.S., Koo H.J., Lee W. J. Chromatogr. A. 837:1999;75-82.
9. Kontos Z., Huszthy P., Bradshaw J.S., Izatt R.M. Tetrahedron: Asymmetry. 10:1999;2087-2099.
10. Horváth G., Huszthy P., Szarvas S., Szókán G., Redd J.T., Bradshaw J.S., Izatt R.M. Ind. Eng. Chem. Res. 39:2000;3576-3581.
11. Hyun M.H., Han S.C., Lipshutz B.H., Shin Y.J., Welch C.J. J. Chromatogr. A. 959:2002;75-83.
12. Hirose K., Ogasahara K., Nishioka K., Tobe Y., Naemura K. J. Chem. Soc., Perkin Trans. 2. 2000;1984-1993.
13. Naemura K., Matsunaga K., Fuji J., Ogasahara K., Nishikawa Y., Hirose K., Tobe Y. Anal. Sci. 14:1998;175-182.
14. Hirose K., Fuji J., Kamada K., Tobe Y., Naemura K. J. Chem. Soc., Perkin Trans. 2. 1997;1649-1657.
15. Huszthy P., Bradshaw J.S., Zhu C.Y., Izatt R.M., Lifson S. J. Org. Chem. 1991;3330-3336.
16. Kaneda T., Ishizaki Y., Misumi S., Kai Y., Hirao G., Kasai N. J. Am. Chem. Soc. 110:1988;2970-2972.
17. The addition of TEA effects to improve sharpness of peaks. The reason for this additive effect is not clear.
18. The chromatographic conditions of CSPs 1 and 2 for each amine shown here were not optimised.
19. Hirose K. J. Incl. Phenom. Macrocyclic Chem. 39:2001;193-209.
20. The CSPs 1 and 2 can be used for the separation of other primary amines and amino acids, such as norephedrine, phenylalanine, and alaninol, which exhibit separation factors (α) 1.32, 1.24, 1.07 on CSP 1 and 1.47, 1.45, 1.18 on CSP 2, respectively. Chromatographic conditions: flow rate=0.7 ml/min, 25°C, hexane/iso-PrOH/MeOH/TFA=80/15/5/0.5 for the separation of alaninol, hexane/EtOH/TFA=70/30/0.5 for the separation of other amines.