Extremely High Enantioselective Redox Reaction of Ketones and Alcohols Catalyzed by RuCl2(PPh3)(oxazolinylferrocenylphosphine)

Organometallics

Volumn 18, Issue 12, 1999, Pages 2291-2293

  Nishibayashi, Yoshiaki ^a   Takei, Izuru ^a   Uemura, Sakae ^b   Hidai, Masanobu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000898101     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990210o     Document Type: Article

References (43)

1. (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
2. (b) Ohkuma, T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
3. (c) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. Engl. 1998, 37, 1100-1103.
4. (d) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, Y. Angew. Chem., Int. Ed. Engl. 1998, 57, 1703-1707.
5. (a) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051-1069, and references therein,
6. (b) Evans, D. A.; Nelson, S. G.; Gagne, M. R.; Muci, A. R. J. Am. Chem Soc. 1993, 115, 9800-9801.
7. (c) Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381-1384.
8. (d) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102, and references therein,
9. (e) Sammakia, T.; Stangeland, E. L. J. Org. Chem. 1997, 62, 6104-6105.
10. (f) Bernard, M.; Guiral, V.; Delbecq, F.; Fache, F.; Sautet, P.; Lemaire, M. J. Am. Chem. Soc. 1998, 120, 1441-1446.
11. (g) Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817-3818.
12. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (d) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807.
13. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (d) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807.
14. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (d) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807.
15. For recent examples, see: (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500-508. (b) Carter, M. B.; Schiott, B.; Gutierrez, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 11667-11670. (c) Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 111-113. (d) Herrmann, W. A.; Goossen, L. J.; Kücher, C.; Artus, G. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807.
16. (a) Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486-5688.
17. (b) Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura, S. Chem. Commun. 1986, 847-848.
18. (c) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375-1376.
19. (d) Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Ohe, K.; Uemura, S. Organometallics 1996, 15, 370-379.
20. (e) Nishibayashi, Y.; Singh, J. D.; Arikawa, Y.; Uemura, S.; Hidai, M. J. Organomet. Chem. 1997, 531, 13-18.
21. (a) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553.
22. (b) Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 2145-2147.
23. (c) Ford, A.; Woodward, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 335-336
24. For reviews, see: (a) Biotransformations in Organic Chemistry; Faber, K., Ed.; Springer-Verlag: New York, 1992. (b) Enzymes in Synthetic Organic Chemistry; Wong, C. H., Whitesides, G. M., Eds.; Pergamon Press: Oxford, 1994. (c) Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957-8964, and references therein.
25. For reviews, see: (a) Biotransformations in Organic Chemistry; Faber, K., Ed.; Springer-Verlag: New York, 1992. (b) Enzymes in Synthetic Organic Chemistry; Wong, C. H., Whitesides, G. M., Eds.; Pergamon Press: Oxford, 1994. (c) Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957-8964, and references therein.
26. For reviews, see: (a) Biotransformations in Organic Chemistry; Faber, K., Ed.; Springer-Verlag: New York, 1992. (b) Enzymes in Synthetic Organic Chemistry; Wong, C. H., Whitesides, G. M., Eds.; Pergamon Press: Oxford, 1994. (c) Nakamura, K.; Matsuda, T. J. Org. Chem. 1998, 63, 8957-8964, and references therein.
27. Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529-13530; xylbinap = 2, 2′-bis(di-3.5xylylphosphino)-1,1′-binaphthyl.
28. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
29. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
30. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
31. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
32. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
33. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
34. 8e-g (e) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10-11. (f) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002-6003. (g) Sammakia, T.; Latham, H. A. J. Org. Chem. 1998, 61, 1629-1635.
35. Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1998, 17, 3420-3422.
36. Arikawa, Y.; Ueoka, M.; Matoba, K.; Nishibayashi, Y.; Hidai, M.; Uemura, S. J. Organomet. Chem. 1999, 572, 163-168.
37. (a) Chowdhury, R. L.; Bäckvall, J.-E. J. Chem. Soc., Chem. Commun. 1991, 1063-1064.
38. (b) Aranyos, A.; Csjernyik, G.; Szabo, K. J.; Bäckvall, J.-E. Chem. Commun. 1999, 351-352.
39. 6/'PrOH solution suggested the formation of two ruthenium dihydride complexes.
40. For a short review: Fehring, V.; Selke, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1827-1830.
41. PennPhos =P,P′-1,2-phenylenebis(endo-2,5-dialkyl-7-phosphabicyclo[2.2.1]heptanes.
42. s, the selectivity factor = (rate of fast-reacting enantiomer)/(rate of slow-reacting enantiomer). For a review, see: Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56, and references therein.
43. Hashiguchi, S.; Fujii, A.; Haack, K -J.; Matsumura, K.; Ikariya, T.; Noyon, R. Angew. Chem.. Int. Ed. Engl. 1997, 36, 288-290.