Chiral drugging: Chiral activator-induced enantiomer selective activation of racemic catalyst for asymmetric amplifying catalysis

Enantiomer

Volumn 1, Issue 1, 1996, Pages 69-73

  Matsukawa, Satoru ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Aldol reaction; Chiral activator; Chiral booster; Chiral drugging; Chiral titanium catalyst; Enantiomer selective activation

Indexed keywords

EID: 0002227151     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (39)

1. Reviews: (a) Kagan, H. B. Asymmetric Synthesis Georg Thieme Verlag: Stuttgart, 1996.
2. (b) Advances in Catalytic Processes: Asymmetric Chemical Transformations Doyle, M. P., Ed.; JAI Press: Greenwich, Connecticut, 1995, Vol. 1.
3. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis Weily: New York, 1994.
4. (d) Catalytic Asymmetric Synthesis Ojima, I., Ed.; VCH: New York, 1993.
5. (e) Asymmetric Catalysis Bosnich, B., Ed.; Martinus Nijhoff: Dordrecht, 1986.
6. (f) Kagan, H. B. Comprehensive Organic Chemistry Pergamon: Oxford, 1982; Vol. 8.
7. Reviews: (a) Guillaneux, D.; Zhao, S.-H.; Samuel, O.; Rainford, D.; Kagan, H. B. J. Am. Chem. Soc. 1994, 116 9430.
8. Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agani, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.
9. (b) Noyori, R.; Kitamura, Angew. Chem. Int. Ed. Engl. 1991, 30, 49.
10. (c) Mikami, K.; Terada, M. Tetrahedron 1992, 48, 5671.
11. Faller, J. W.; Parr, J. J. Am. Chem. Soc. 1993, 115 804.
12. Also see: Alcock, N. W.; Brown, J. M.; Maddox, P. J. J. Chem. Soc., Chem. Commun. 1986, 1532;
13. Brown, J. M.; Maddox, P. J. Chirality 1991, 3, 345.
14. Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111 789.
15. In the construction of a chiral catalyst from the achiral procatalyst, Sharpless et al emphasize the importance of chiral ligand acceleration of the reactions. For the review, see: Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. Int. Ed. Engl. 1995, 34, 1059.
16. Prof. D. Enders suggested the German expression of "Belebung" for the English of activator or animator, during the stay in our Tokyo Institute of Technology.
17. Reviews: (a) Mukaiyama, T. Org. React. 1982, 28, 203.
18. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
19. (c) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984, Vol. 3; Chap. 2.
20. (d) Masamune, S.; Choy, W.; Peterson, J.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1986, 24, 1.
21. (e) Paterson, I.; Goodman, J. M.; Lister, M. A.; Schumann, R. C.; McClure, C. K.; Norcross, R. D. Tetrahedron 1990, 46, 4663.
22. (f) Gennari, C. In Comprehensive Organic Syntliesis; Trost, B. M.; Fleming, I. Ed.; Pergamon Press: Oxford, 1991, Vol. 2; Chap. 2.4.
23. (g) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Ed.; Pergamon Press: Oxford, 1991, Vol. 2; Chap. 1.7
24. (a) Kobayashi, S.; Uchiro, H.; Fujishita, Y.; Shiina, I.; Mukaiyama, T. J. Am. Chem. Soc. 1991, 113, 4247.
25. (b) Parmee, E. R.; Tempkin, O.; Masamune, S.; Abiko, A. J. Am. Chem. Soc. 1991, 113, 9365.
26. (c) Furuta, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041.
27. (d) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
28. (e) Kiyooka, S.; Kaneko, Y.; Kume, K. Tetrahedron Lett. 1992, 33, 4927.
29. (f) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039.
30. (g) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
31. Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077.
32. Matsukawa, S.; Mikami, K. Tetrahedron Assymmetry. 1995, 6, 2571.
33. iPr)2 catalyst: Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363.
34. Reviews on asymmetric catalysis by chiral titanium complexes: (a) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
35. (b) Mikami, K.; Terada, M.; Narisawa, S.; Nakai, T. Synlett 1992, 255.
36. (c) Mikami, K.; Terada, M.; Nakai, T. J. Synth. Org. Chem. Jpn. 1991, 49, 566.
37. (d) Reetz, M. T. Organotitanium Reagents in Organic Synthesis, Springer-Verlag: Berlin, 1986.
38. (e) Seebach, D.; Weidmann, B.; Widler, L. In Modern Synthetic Methods, Vol. 3; Scheffold, R., Ed. Springer: Berlin, 1983. p 217.
39. 13C NMR data. The titanium complex derived from racemic BINOL shows the other species in a ratio of 1:1, due to the additional non-symmetric hetero-chiral (R/S)-BINOLate-Ti dimer (B). Furthermore, the titanium complex derived from 50% ee of (R)-BINOL shows the homo- and hetero-chiral species in a statistical ratio of ca. 1.5 : 1.