Kinetic resolution when the chiral auxiliary is not enantiomerically pure: Normal and abnormal behavior

Journal of the American Chemical Society

Volumn 121, Issue 40, 1999, Pages 9299-9306

  Luukas, Timo O ^a   Girard, Christian ^a   Fenwick, David R ^a,b   Kagan, Henri B ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

REAGENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY;

EID: 0033552241     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990793t     Document Type: Article

References (38)

1. Kagan, H. B.; Fiaud, J. C. Kinetic Resolution. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1988; Vol. 18, pp 249-330.
2. Sih, C. J.; Wu, S. H. Resolution of Enantiomers via Biocatalysis. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1989; Vol. 19, pp 63-125.
3. sm with conversion.
4. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240.
5. (a) El Baba, S.; Poulin, J. C.; Kagan, H. B. Tetrahedron 1984, 40, 4275-4284.
6. (b) Kagan, H. B. Croat. Chem. Acta 1996, 69, 669-680.
7. aux.
8. Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353-2357.
9. For some reviews on NLE in catalysis see refs 9 and 10.
10. Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Tetrahedron: Asymmetry 1997, 8, 2997-3017.
11. Girard, C.; Kagan, H. B. Angew. Chem. 1998, 110, 3088-3127. Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922-2959.
12. Girard, C.; Kagan, H. B. Angew. Chem. 1998, 110, 3088-3127. Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922-2959.
13. Guillaneux, D.; Zhao, S. H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116, 9430-9439.
14. (a) Kitamura, M.; Okada, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
15. (b) Yamakawa, M.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 6327-6335.
16. (c) Kitamura, M.; Suga, S.; Oka, H.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 9800-9809.
17. 15 Our approach, mainly devoted to catalytic reactions on racemic substrates, is different from refs 14 and 15, since its aim is to discuss deviations with respect to the predictions given by a classical kinetic treatment.
18. de Min, M.; Levy, G.; Micheau, J. C. J. Chim. Phys. 1988, 85, 607-608.
19. Ismagilov, R. F. J. Org. Chem. 1998, 63, 3772-3774.
20. Alberts, A. H.; Wynberg, H. J. Am. Chem. Soc. 1989, 111, 7265-7266.
21. 14
22. Sepulchre, M.; Spassky, N.; Sigwalt, P. Isr. J. Chem. 1976-77, 15, 33-38.
23. Brandt, J.; Jochum, C.; Ugi, I. Tetrahedron 1977, 33, 1353-1363.
24. Horeau, A. In Stereochemistry Fundamentals and Methods; Kagan, H. B., Ed.; Thieme Verlag: Stuttgart, 1977; Vol. 3, pp 51-94.
25. Horeau, A. Bull. Soc. Chim. Fr. 1967, 117-124.
26. Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624-7626.
27. Brunel, J. M.; Luukas, T. O.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 1941-1946.
28. Hayashi, M.; Miwata, H.; Oguni, N. J. Chem. Soc., Perkin Trans. 1 1991, 1167-1171.
29. Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086-8088.
30. sm are given in the Supporting Information.
31. For definition of indexes of asymmetric amplification in asymmetric catalysis see the discussion in ref 28.
32. Kagan, H. B.; Fenwick, D. R. Asymmetric Amplification. In Topics in Stereochemistry; Denmark, S., Ed.; John Wiley & Sons: New York, 1999; Vol. 22, pp 257-296.
33. 30b The same concepts should apply to kinetic resolution.
34. (a) Blackmond, D. J. Am. Chem. Soc. 1997, 119, 12934-12939.
35. (b) Blackmond, D. J. Am. Chem. Soc. 1998, 120, 13349-13353.
36. Luukas, T. O.; Girard, C.; Fenwick, D.; Kagan H. B. Manuscript in preparation.
37. 31
38. Ali, M.; Stevens, W. Synthesis 1997, 764-768.