Complete Optical Resolution by Differential Complexation in Solution between a Chiral Cyclic Polyether and an α-Amino Acid

Journal of the American Chemical Society

Volumn 95, Issue 9, 1973, Pages 3021-3023

  Helgeson, Roger C ^a   Koga, Kenji ^a   Tintko, Joseph M ^a   Cram, Donald J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947085794     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00790a052     Document Type: Article

References (38)

1. F. Cramer and W. Dietsche, Chem. Ber., 92, 378, 1739 (1959).
2. F. Cramer and W. Kampe, J. Amer. Chem. Soc. 87, 1115 (1965).
3. F. Cramer, Angew. Chem., Int. Ed. Engl., 5, 601 (1966).
4. R. L. van Etten, G. A. Clowes, J. F. Sebastian, and M. L. Bender, J. Amer. Chem. Soc., 89, 3253 (1967).
5. R. Breslow and P. Campbell, J. Amer. Chem. Soc., 91, 3085 (1969).
6. K. Flohr, R. M. Patón, and E. T. Kaiser, Chem. Commun., 1621 (1971).
7. A. K. Colter, F. F. Guzik, and S. H. Hui, J. Amer. Chem. Soc., 88, 5754 (1966).
8. R. Hershfield and M. L. Bender, J. Amer. Chem. Soc., 94, 1376 (1972).
9. M. S. Newman, W. B. Lutz, and D. Lednicer, J. Amer. Chem. Soc., 77, 3420 (1955).
10. M. S. Newman, W. B. Lutz, and D. Lednicer, J. Amer. Chem. Soc., 78, 2467 (1956).
11. M. S. Newman, “Steric Effects in Organic Chemistry,” Wiley, New York, N. Y., 1956, pp 472-478.
12. A. C. D. Newman and H. M. Powell, J. Chem. Soc., 3747 (1952).
13. M. Schlenk, Jr., Experientia, 8, 337 (1952).
14. D. R. Buss and T. Vermeulen, Ind. Eng. Chem., 60, 12 (1968).
15. P. H. Boyle, Quart. Rev., Chem. Soc., 323 (1971).
16. G. Losse and K. Kuntze, Z. Chem., 10, 22 (1970).
17. B. Feibush and E. Gil-Av, Tetrahedron, 26, 1361 (1970).
18. W. Parr, J. Pleterski, C. Yang, and E. Bayer, J. Chromatogr. Sci., 9, 141 (1971).
19. M. Mikolajezyk, J. Drabowicz, and F. Cramer, Chem. Commun., 317 (1971).
20. P. Benschop and G. R. Van den Berg, Chem. Commun., 1431 (1970).
21. N. S. Bowman, G. T. McCloud, and G. K. Schweitzer, J. Amer. Chem. Soc., 90, 3848 (1968).
22. J. D. Morrison and H. S. Mosher, “Asymmetric Organic Reactions,” Prentice-Hall, Englewood Cliffs, N. J., 1971, pp 16-17.
23. V. O. G. Klingmüller and G. Gedenk, Nature (London), 179, 367 (1957).
24. K. Bauer, H. Falk, and u. K. Schlögl, Monatsh. Chem., 99, 2186 (1968).
25. S. J. Romano, K. H. Wells, H. L. Rothbart, and W. Rieman, III, Talanta, 16, 581 (1969).
26. S. H. Wilen, Top. Stereochem., 6, 107 (1972).
27. R. C. Helgeson, J. M. Timko, and D. J. Cram, J. Amer. Chem. Soc., 95, 3023 (1973).
28. W. M. Stanley and R. Adams, Reel. Trav. Chim. Pays-Bas, 48, 1035 (1929).
29. K. Weil and W. Kuhn, Helv. Chim. Acta, 27, 1648 (1944).
30. H. J. Barber and K. Gaimster, J. Appl. Chem., 2, 565 (1952).
31. H. Akimoto, T. Shioiri, Y. Iitaka, and S. Yamada, Tetrahedron Lett., 97 (1968).
32. H. Akimoto, T. Shioiri, Y. Iitaka, and S. Yamada, Tetrahedron Lett., 4617 (1971).
33. H. Akimoto and Y. Iitaka, Acta Crystallogr., Sect. B, 25, 1491 (1969).
34. I. Hanazaki and H. Akimoto, J. Amer. Chem. Soc., 94, 4102 (1972).
35. H. Akimoto and S. Yamada, Tetrahedron, 27, 5999 (1971).
36. E. P. Kyba, K. Koga, L. R. Sousa, M. R. Siegel, and D. J. Cram, J. Amer. Chem. Soc., 95, 2692 (1973).
37. E. P. Kyba, M. G. Siegel, L. R. Sousa, G. D. Y. Sogah, and D. J. Cram, J. Amer. Chem. Soc., 95, 2691 (1973).
38. J. P. Greenstein and M. Winitz, “Chemistry of the Amino Acids,” Wiley, New York, N. Y., 1961, p 116.