Novel chiral ligands, diferrocenyl dichalcogenides and their derivatives, for rhodium- and iridium-catalyzed asymmetric hydrosilylation

Organometallics

Volumn 15, Issue 1, 1996, Pages 370-379

  Nishibayashi, Yoshiaki ^a   Segawa, Kyohei ^a   Singh, Jai Deo ^a   Fukuzawa, Shin Ichi ^b   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

^b CHUO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007023980     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om950533u     Document Type: Article

References (52)

1. For an example : Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds; VCH: Weinheim, Germany, 1993.
2. (a) Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
3. (b) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972, 10.
4. (c) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Backman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
5. For examples: (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. (b) Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 1.
6. For examples: (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345. (b) Takaya, H.; Ohta, T.; Noyori, R. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 1.
7. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashims, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138.
8. Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 867.
9. (a) Hayashi, T.; Kawamura, N,; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876.
10. (b) Hayashi, T.; Kawamura, N.; Ito, Y. Tetrahedron Lett, 1988, 29, 5969.
11. For an example: Hayashi, T. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 7.1.
12. For an example: Sawamura, M.; Ito, Y. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 7.2.
13. (a) Nishibayashi, Y.; Singh, J. D.; Uemura, S.; Fukuzawa, S. Tetrahedron Lett. 1994, 35, 3115.
14. (b) Nishibayashi, Y.; Singh, J. D.; Fukuzawa, S.; Uemura, S. J. Org. Chem. 1995, 60, 4114.
15. (c) Nishibayasahi, Y.; Singh, J. D.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Perkin Trans. 1, in press.
16. For examples (a) Murray, S. G.; Hartley, F. R. Chem. Rev. 1981, 81, 365. (b) Gysling, H. J. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1986; Vol. 1, p 679.
17. For examples (a) Murray, S. G.; Hartley, F. R. Chem. Rev. 1981, 81, 365. (b) Gysling, H. J. The Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1986; Vol. 1, p 679.
18. Preliminary communication: Nishibayashi, Y.; Singh, J. D.; Segawa, K.; Fukuzawa, S.; Uemura, S. J. Chem. Soc., Chem. Commun. 1994, 1375.
19. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5396. Marquarding, D.; Burghard, H.; Ugi, I.; Urban, R.; Klusacek, H. J. Chem. Res. (S) 1977, 82.
20. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5396. Marquarding, D.; Burghard, H.; Ugi, I.; Urban, R.; Klusacek, H. J. Chem. Res. (S) 1977, 82.
21. The sulfur analogue of 8 was also formed and similarly fully characterized.
22. Rebiere, F.; Riant, O.; Ricard, L.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1993, 32, 568.
23. Singh, A. K.; Srivastava, V. J. Coord. Chem. 1992, 27, 237.
24. (a) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
25. (b) Breutel, C.; Pregosin, P. S.; Salzmann, R.; Togni, A. J. Am. Chem. Soc. 1994, 116, 4067.
26. (a) Ferreira, J. T. B.; Oliveira, A. R. M.; Comasseto, J. V. Tetrahedron Lett. 1992, 33, 915.
27. (b) Nishibayashi, Y.; Chiba, T,; Singh, J. D.; Uemura S.; Fukuzawa, S. J. Organomet. Chem. 1994, 473, 205.
28. Dumont, W.; Poulin, J. C.; Dang, T.-P.; Kagan, H. B. J. Am. Chem. Soc. 1973, 95, 8295.
29. (a) Brunner, H.; Becker, R.; Riepl, G. Organometallics 1984, 3, 1354.
30. (b) Brunner, H.; Oberman, U. Chem. Ber. 1989, 122, 499.
31. (c) Brunner, H.; Brandi, P. Tetrahedron Asymmetry 1991, 931.
32. (a) Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
33. (b) Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Nakamura, T.; Itoh, K. J. Org. Chem. 1992, 57, 4306.
34. The transition metal-catalyzed asymmetric hydrosilylation of ketones has been well studied. For an example: Brunner, H.; Nishiyama, H.; Itoh, K. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 6.
35. (a) Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 425.
36. (b) Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett. 1976, 4531.
37. Ojima, I.; Kogure, T.; Kumagai, M. J. Org. Chem. 1977, 42, 1671.
38. (a) Zassinovich, G.; Bettella, R.; Mestroni, G.; Bresciani-Pahor, N.; Geremia, S.; Randaccio, L. J. Organomet. Chem. 1989, 370, 187.
39. (b) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232.
40. Mashima, K.; Akutagawa, T.; Zhang, X.; Takaya, H.; Taketomi, T.; Kumobayashi, H.; Akutagawa, S. J. Organomet. Chem. 1992, 428, 213.
41. Kinting, A.; Kreuzfeld, H. J.; Abicht, H. P. J. Organomet. Chem. 1989, 370, 343.
42. (a) Langlois, N.; Dang, T. P.; Kagan, H. B. Tetrahedron Lett. 1973, 4865.
43. (b) Kagan, H. B.; Langlois, N.; Dang, T. P. J. Organomet. Chem. 1975, 90, 353.
44. (c) Becker, R.; Brunner, H.; Mahboobi, S.; Wiegrebe, W. Angew. Chem., Int. Ed. Engl. 1985, 24, 995.
45. (a) Collman, J. P.; Rothrock, R. K.; Sen, J. P.; Tullius, T. D.; Hodgson, K. O. Inorg. Chem. 1976, 15, 2947.
46. (b) Collman, J. P.; Rothrock, R. K.; Stark, R. A. Inorg. Chem. 1977, 16, 437.
47. Gokel, G.; Ugi, I. J. Chem. Educ. 1972, 49, 82.
48. (a) Honeychuck, R. V.; Okoroafor, M. O.; Shen, L. H.; Brubaker, C. H., Jr. Organometallics 1986, 5, 482.
49. (b) Okoroafor, M. O.; Ward, D. L.; Brubaker, C. H., Jr. Organometallics 1988, 7, 1504.
50. 4: Bochmann, M; Webb, K. J.; Hursthouse, M. B.; Mazid, M. J. Chem. Soc., Dalton Trans. 1991, 2317.
51. Kasai, M.; Froussios, C.; Ziffer, H. J. Org. Chem. 1983, 48, 459.
52. Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262.