BINAP: An Efficient Chiral Element for Asymmetric Catalysis

Accounts of Chemical Research

Volumn 23, Issue 10, 1990, Pages 345-350

  Noyori, Ryoji ^a   Takaya, Hldemasa ^b,c  

^a NAGOYA UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001247165     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar00178a005     Document Type: Article

References (65)

1. For the present state of this subject, see: Noyori, R. Science 1990, 248, 1194.
2. Noyori, R.; Kitamura, M. In Modern Synthetic Methods 1989; Scheffold, R., Ed.; Springer-Verlag: Berlin, 1989; p 115.
3. Blystone, S. L. Chem. Rev. 1989, 89, 1663.
4. Ojima, I.; Clos, N.; Bastos, C. Tetrahedron 1989, 45, 6901.
5. Brunner, H. Top. Stereochem. 1988, 18, 129.
6. Accomplishments up to the early 1980s: Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5.
7. Kagan, H. B. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: London, 1982; Vol. 8, p 463.
8. Asymmetric Catalysis; Bosnich, B., Ed.; NATO ASI Series; Martinus Nijhoff Publishers: Dordrecht, 1986.
9. Noyori, R.; Suga, S.; Kawai, K.; Okada, S.; Kitamura, M. Pure Appl. Chem. 1988, 60, 1597.
10. Kitamura, M.; Okada, S.; Suga, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028.
11. Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877.
12. Noyori, R.; Kitamura, M. Angew. Chem., in press.
13. Noyori, R.; Takaya, H. Chem. Scr. 1985, 25, 83.
14. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
15. Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245.
16. Brown, K. J.; Berry, M. S.; Waterman, K. C.; Lingenfelter, D.; Murdoch, J. R. J. Am. Chem. Soc. 1984, 106, 4717.
17. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
18. Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1988, 67, 20.
19. Review: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
20. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc. 1972, 94, 6429.
21. For example: Cram, D. J.; Cram, J. M. Acc Chem. Res. 1978, 11, 8.
22. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
23. Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717.
24. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem. 1988, 27, 566.
25. Mashima, K.; Kusano, K.; Ohta, T.; Noyori, R.; Takaya, H. J. Chem. Soc, Chem. Commun. 1989, 1208.
26. Toriumi, K.; Ito, T.; Takaya, H.; Souchi, T.; Noyori, R. Acta Crystallogr., Sect. B 1982, B38, 807.
27. Tani, K.; Yamagata, T.; Tatsuno, Y.; Yamagata, Y.; Tomita, K.; Akutagawa, S.; Kumobayashi, H.; Otsuka, S. Angew. Chem., Int. Ed. Engl. 1985, 24, 217.
28. Horner, L.; Siegel, H.; Büthe, H. Angew. Chem., Int. Ed. Engl. 1968, 7, 942.
29. Knowles, W. S.; Sabacky, M. J. J. Chem. Soc, Chem. Commun. 1968, 1445.
30. Knowles, W. S. J. Chem. Educ. 1986, 63, 222.
31. Halpern, J. In Asymmetrie Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, Chapter 2.
32. Koenig, K. E. Asymmetrie Synthesis Chapter 3.
33. Kagan, H. B. Bull. Soc Chim. Fr. 1988, 846.
34. Noyori, R. Chimia 1988, 42, 215.
35. Noyori, R. Chem. Soc. Reu. 1989, 18, 187.
36. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174.
37. Kawano, H.; Ikariya, T.; Ishii, Y.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumobayashi, H. J. Chem. Soc, Perkin Trans. 1989, 1571.
38. Muramatsu, H.; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc, Chem. Commun. 1989, 769.
39. Review on functional group directed hydrogenation: Brown, J. M. Angew. Chem., Int. Ed. Engl. 1987, 26, 190.
40. Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; Takaya, H.; Akutagawa, S.; Sayo, N.; Saito, T.; Taketomi, T.; Kumobayashi, H. J. Am. Chem. Soc 1989, 111, 9134.
41. Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117.
42. Kitamura, M.; Hsiao, Y.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829.
43. Takaya, H.; Ohta, T.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Inoue, S.; Kasahara, I.; Noyori, R. J. Am. Chem. Soc. 1987, 109, 1596, 4129.
44. Inoue, S.; Osada, M.; Koyano, K.; Takaya, H.; Noyori, R. Chem. Lett. 1985, 1007.
45. Imperiali, B.; Zimmerman, J. W. Tetrahedron Lett. 1988, 29, 5343.
46. Kitamura, M.; Nagai, K.; Hsiao, Y.; Noyori, R. Tetrahedron Lett. 1990, 31, 549.
47. Shih, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Heterocycles 1984, 21, 29.
48. BINAP-Rh-catalyzed hydrogénation of a chiral α,β-unsaturated carboxylic ester: Evans, D. A.; Morrissey, M. M.; Dow, R. L. Tetrahedron Lett. 1985, 26, 6005.
49. Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R.; Takaya, H. J. Org. Chem. 1988, 53, 708.
50. Noyori, R. Chem. Br. 1989, 25, 883.
51. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takava, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
52. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
53. See also: Schreiber, S. L.; Kelly, S. E.; Porco, J. A., Jr.; Sammakia, T.: Suh, E. M. J. Am. Chem. Soc. 1988, 110, 6210.
54. Kitamura, M.; Ohkuma, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1988, 29, 1555.
55. Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc, Chem. Commun. 1988, 87.
56. Nishi, T.; Kitamura, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett. 1988, 29, 6327.
57. Kitamura, M.; Ohkuma, T.; Tokunaga, M.; Noyori, R. Tetrahedron Asymmetry 1990, 1, 1.
58. Tani, K.; Yamagata, T.; Otsuka, S.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R. J. Chem. Soc, Chem. Commun. 1982, 600.
59. Tani, K.; Yamagata, T.; Akutagawa, S.; Kumobayashi, H.; Taketomi, T.; Takaya, H.; Miyashita, A.; Noyori, R.; Otsuka, S. J. Am. Chem. Soc 1984, 106, 5208.
60. Takabe, K.; Uchiyama, Y.; Okisaka, K.; Yamada, T.; Katagiri, T.; Okazaki, T.; Oketa, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Lett. 1985, 26, 5153.
61. Inoue, S.; Takaya, H.; Tani, K.; Otsuka, S.; Sato, T.; Noyori, R. J. Am. Chem. Soc. 1990, 112, 4897.
62. Kitamura, M.; Manabe, K.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4719.
63. Ishii, Y.; Sasaki, T.; Ikariya, T.; Saburi, M.; Yoshikawa, S. Nippon Kagaku Kaishi 1985, 465.
64. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 3426.
65. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 5579.