Resolution of trans-cyclohexane-1,2-diamine and determination of the enantiopurity using chiral solid-phase HPLC techniques and polarimetry

Journal of Chemical Education

Volumn 75, Issue 11, 1998, Pages 1459-1462

  Walsh, Patrick J ^a   Smith, Diane K ^a   Castello, Chris ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040266021     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed075p1459     Document Type: Article

References (25)

1. Liska, K. Drugs and the Human Body; Macmillan: New York, 1990. Koskinen, A. Asymmetric Synthesis of Natural Products; Wiley: New York, 1993.
2. Liska, K. Drugs and the Human Body; Macmillan: New York, 1990. Koskinen, A. Asymmetric Synthesis of Natural Products; Wiley: New York, 1993.
3. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, The Netherlands, 1986. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Handbook of Enantioselective Catalysts; Brunner, H.; Zettlmeier, W., Eds.; VCH: New York, 1993. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, The Netherlands, 1986. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Handbook of Enantioselective Catalysts; Brunner, H.; Zettlmeier, W., Eds.; VCH: New York, 1993. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
5. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, The Netherlands, 1986. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Handbook of Enantioselective Catalysts; Brunner, H.; Zettlmeier, W., Eds.; VCH: New York, 1993. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
6. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, The Netherlands, 1986. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Handbook of Enantioselective Catalysts; Brunner, H.; Zettlmeier, W., Eds.; VCH: New York, 1993. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
7. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, The Netherlands, 1986. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Handbook of Enantioselective Catalysts; Brunner, H.; Zettlmeier, W., Eds.; VCH: New York, 1993. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
8. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1985. Asymmetric Catalysis; Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, The Netherlands, 1986. Whitesell, J. K. Chem. Rev. 1989, 89, 1581. Handbook of Enantioselective Catalysts; Brunner, H.; Zettlmeier, W., Eds.; VCH: New York, 1993. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
9. Stinson, S. C. Chem. Eng. News 1994, 72(Sep 19), 38.
10. Stinson, S. C. Chem. Eng. News 1995, 73(Oct 9), 44.
11. Optical Resolutions Procedures for Chemical Compounds, Vol. 1-4; Newman, P., Ed.; Optical Resolution Information Center: New York, 1993.
12. For example, see Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Longman Scientific & Technical: New York, 1989.
13. (a) Gaslbøl, F.; Steenbøl, P.; Sørensen, B. S. Acta Chem. Scand. 1972, 26, 3605.
14. For recent resolution procedures see (b) Larrow, J. F.; Jacobsen, E. N.; Gao. Y.; Hong, Y.; Nie, X.; Zepp, C. M. J. Org. Chem. 1994, 59, 1939.
15. Bennani, Y. L.; Hanessian, S. Chem. Rev. 1997, 97, 3161.
16. Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425. Irie, N.; Ito, Y.; Katsuki, T. Syn. Lett. 1994, 255.
17. Zhang, W.; Lee, N. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 425. Irie, N.; Ito, Y.; Katsuki, T. Syn. Lett. 1994, 255.
18. Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326.
19. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayshi, S. Tetrahedron 1992, 48, 5691. Rozema, M. J.; Eisenberg, C.; Lütjens, H.; Ostwalt, R.; Belyk, K.; Knochel, P. Tetrahedron Lett. 1993, 34, 3115.
20. Takahashi, H.; Kawakita, T.; Ohno, M.; Yoshioka, M.; Kobayshi, S. Tetrahedron 1992, 48, 5691. Rozema, M. J.; Eisenberg, C.; Lütjens, H.; Ostwalt, R.; Belyk, K.; Knochel, P. Tetrahedron Lett. 1993, 34, 3115.
21. Trost, B. M.; Krueger, A. C.; Bunt, R. C.; Zambrano, J. J. Am. Chem. Soc. 1996, 118, 6521.
22. Imai, N.; Takahashi, H.; Kobayashi, S. Chem. Lett. 1994, 177. Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045. Denmark, S. E.; Christenson, B. I.; Coe, D. M.; O'Connor. S. P. Tetrahedron Lett. 1996, 36, 2215.
23. Imai, N.; Takahashi, H.; Kobayashi, S. Chem. Lett. 1994, 177. Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045. Denmark, S. E.; Christenson, B. I.; Coe, D. M.; O'Connor. S. P. Tetrahedron Lett. 1996, 36, 2215.
24. Imai, N.; Takahashi, H.; Kobayashi, S. Chem. Lett. 1994, 177. Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045. Denmark, S. E.; Christenson, B. I.; Coe, D. M.; O'Connor. S. P. Tetrahedron Lett. 1996, 36, 2215.
25. Asymmetric Synthesis; Aitken, R. A.; Kilényi, S. N. Eds.; Blackie Academic & Professional: London, 1992.