Asymmetric hydrosilylation of olefins catalyzed by MOP-palladium complexes

Acta Chemica Scandinavica

Volumn 50, Issue 3, 1996, Pages 259-266

  Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000015844     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.50-0259     Document Type: Article

References (78)

1. For recent reviews: (a) Brunner, H. Synthesis (1988) 645 (b) H. Top. Stereochem 18 (1988) 129 (c) Noyori, R. and Kitamura, In: Schefford, R., Ed., Modern Synthetic Methods, Springer-Verlag: New York 1989, Vol. 5. p. 115 (d) Ojima, I., Clos, N. and Bastos, C. Tetrahedron 45 (1989) 6901 (e) Ojima, I. Catalytic Asymmetric Synthesis, VCH, New York 1993 (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
2. For recent reviews: (a) Brunner, H. Synthesis (1988) 645 (b) H. Top. Stereochem 18 (1988) 129 (c) Noyori, R. and Kitamura, In: Schefford, R., Ed., Modern Synthetic Methods, Springer-Verlag: New York 1989, Vol. 5. p. 115 (d) Ojima, I., Clos, N. and Bastos, C. Tetrahedron 45 (1989) 6901 (e) Ojima, I. Catalytic Asymmetric Synthesis, VCH, New York 1993 (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
3. For recent reviews: (a) Brunner, H. Synthesis (1988) 645 (b) H. Top. Stereochem 18 (1988) 129 (c) Noyori, R. and Kitamura, In: Schefford, R., Ed., Modern Synthetic Methods, Springer-Verlag: New York 1989, Vol. 5. p. 115 (d) Ojima, I., Clos, N. and Bastos, C. Tetrahedron 45 (1989) 6901 (e) Ojima, I. Catalytic Asymmetric Synthesis, VCH, New York 1993 (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
4. For recent reviews: (a) Brunner, H. Synthesis (1988) 645 (b) H. Top. Stereochem 18 (1988) 129 (c) Noyori, R. and Kitamura, In: Schefford, R., Ed., Modern Synthetic Methods, Springer-Verlag: New York 1989, Vol. 5. p. 115 (d) Ojima, I., Clos, N. and Bastos, C. Tetrahedron 45 (1989) 6901 (e) Ojima, I. Catalytic Asymmetric Synthesis, VCH, New York 1993 (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
5. For recent reviews: (a) Brunner, H. Synthesis (1988) 645 (b) H. Top. Stereochem 18 (1988) 129 (c) Noyori, R. and Kitamura, In: Schefford, R., Ed., Modern Synthetic Methods, Springer-Verlag: New York 1989, Vol. 5. p. 115 (d) Ojima, I., Clos, N. and Bastos, C. Tetrahedron 45 (1989) 6901 (e) Ojima, I. Catalytic Asymmetric Synthesis, VCH, New York 1993 (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
6. For recent reviews: (a) Brunner, H. Synthesis (1988) 645 (b) H. Top. Stereochem 18 (1988) 129 (c) Noyori, R. and Kitamura, In: Schefford, R., Ed., Modern Synthetic Methods, Springer-Verlag: New York 1989, Vol. 5. p. 115 (d) Ojima, I., Clos, N. and Bastos, C. Tetrahedron 45 (1989) 6901 (e) Ojima, I. Catalytic Asymmetric Synthesis, VCH, New York 1993 (f) Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York 1994.
7. For (R)-2,2′-Bis(diphenylphosphino)-1.1′-binaphthyl see: (a) Takaya, H., Mashima, K., Koyano, K., Yagi, M., Kumobayashi, H., Taketomi, T., Akutagawa, S. and Noyori, R. J Org. Chem. 51 (1986) 629 (b) Noyori, R. Chem. Soc. Rev. 18 (1989) 187 and references cited therein (c) Noyori, R. and Takaya, H. Acc. Chem. Res. 23 (1990) 345 and references cited therein.
8. For (R)-2,2′-Bis(diphenylphosphino)-1.1′-binaphthyl see: (a) Takaya, H., Mashima, K., Koyano, K., Yagi, M., Kumobayashi, H., Taketomi, T., Akutagawa, S. and Noyori, R. J Org. Chem. 51 (1986) 629 (b) Noyori, R. Chem. Soc. Rev. 18 (1989) 187 and references cited therein (c) Noyori, R. and Takaya, H. Acc. Chem. Res. 23 (1990) 345 and references cited therein.
9. For (R)-2,2′-Bis(diphenylphosphino)-1.1′-binaphthyl see: (a) Takaya, H., Mashima, K., Koyano, K., Yagi, M., Kumobayashi, H., Taketomi, T., Akutagawa, S. and Noyori, R. J Org. Chem. 51 (1986) 629 (b) Noyori, R. Chem. Soc. Rev. 18 (1989) 187 and references cited therein (c) Noyori, R. and Takaya, H. Acc. Chem. Res. 23 (1990) 345 and references cited therein.
10. For reviews: (a) Hayashi, T. In: Togni, A., Hayashi, T., Eds. Ferrocenes, VCH, Weinheim 1995, p. 105 (b) Sawamura, M. and Ito, Y. Chem. Rev. 92 (1992) 857 (c) Hayashi, T. Pure Appl. Chem. 60 (1988) 7 (d) Hayashi, T. In: Streith, J., Prinzbach, H. and Schill G., Eds., Organic Synthesis: An Interdisciplinary Challenge, Blackwell Boston 1985, p. 35 (e) Hayashi, T. and Kumada, M. Acc. Chem. Res. 25 (1982) 395 (f) Hayashi, T. and Kumada, M. In: Ishii, Y. and Tsutsui M., Eds.: Fundamental Research in Homogeneous Catalysis, Plenum, New York 1978, Vol. 2, p. 159.
11. For reviews: (a) Hayashi, T. In: Togni, A., Hayashi, T., Eds. Ferrocenes, VCH, Weinheim 1995, p. 105 (b) Sawamura, M. and Ito, Y. Chem. Rev. 92 (1992) 857 (c) Hayashi, T. Pure Appl. Chem. 60 (1988) 7 (d) Hayashi, T. In: Streith, J., Prinzbach, H. and Schill G., Eds., Organic Synthesis: An Interdisciplinary Challenge, Blackwell Boston 1985, p. 35 (e) Hayashi, T. and Kumada, M. Acc. Chem. Res. 25 (1982) 395 (f) Hayashi, T. and Kumada, M. In: Ishii, Y. and Tsutsui M., Eds.: Fundamental Research in Homogeneous Catalysis, Plenum, New York 1978, Vol. 2, p. 159.
12. For reviews: (a) Hayashi, T. In: Togni, A., Hayashi, T., Eds. Ferrocenes, VCH, Weinheim 1995, p. 105 (b) Sawamura, M. and Ito, Y. Chem. Rev. 92 (1992) 857 (c) Hayashi, T. Pure Appl. Chem. 60 (1988) 7 (d) Hayashi, T. In: Streith, J., Prinzbach, H. and Schill G., Eds., Organic Synthesis: An Interdisciplinary Challenge, Blackwell Boston 1985, p. 35 (e) Hayashi, T. and Kumada, M. Acc. Chem. Res. 25 (1982) 395 (f) Hayashi, T. and Kumada, M. In: Ishii, Y. and Tsutsui M., Eds.: Fundamental Research in Homogeneous Catalysis, Plenum, New York 1978, Vol. 2, p. 159.
13. For reviews: (a) Hayashi, T. In: Togni, A., Hayashi, T., Eds. Ferrocenes, VCH, Weinheim 1995, p. 105 (b) Sawamura, M. and Ito, Y. Chem. Rev. 92 (1992) 857 (c) Hayashi, T. Pure Appl. Chem. 60 (1988) 7 (d) Hayashi, T. In: Streith, J., Prinzbach, H. and Schill G., Eds., Organic Synthesis: An Interdisciplinary Challenge, Blackwell Boston 1985, p. 35 (e) Hayashi, T. and Kumada, M. Acc. Chem. Res. 25 (1982) 395 (f) Hayashi, T. and Kumada, M. In: Ishii, Y. and Tsutsui M., Eds.: Fundamental Research in Homogeneous Catalysis, Plenum, New York 1978, Vol. 2, p. 159.
14. For reviews: (a) Hayashi, T. In: Togni, A., Hayashi, T., Eds. Ferrocenes, VCH, Weinheim 1995, p. 105 (b) Sawamura, M. and Ito, Y. Chem. Rev. 92 (1992) 857 (c) Hayashi, T. Pure Appl. Chem. 60 (1988) 7 (d) Hayashi, T. In: Streith, J., Prinzbach, H. and Schill G., Eds., Organic Synthesis: An Interdisciplinary Challenge, Blackwell Boston 1985, p. 35 (e) Hayashi, T. and Kumada, M. Acc. Chem. Res. 25 (1982) 395 (f) Hayashi, T. and Kumada, M. In: Ishii, Y. and Tsutsui M., Eds.: Fundamental Research in Homogeneous Catalysis, Plenum, New York 1978, Vol. 2, p. 159.
15. For reviews: (a) Hayashi, T. In: Togni, A., Hayashi, T., Eds. Ferrocenes, VCH, Weinheim 1995, p. 105 (b) Sawamura, M. and Ito, Y. Chem. Rev. 92 (1992) 857 (c) Hayashi, T. Pure Appl. Chem. 60 (1988) 7 (d) Hayashi, T. In: Streith, J., Prinzbach, H. and Schill G., Eds., Organic Synthesis: An Interdisciplinary Challenge, Blackwell Boston 1985, p. 35 (e) Hayashi, T. and Kumada, M. Acc. Chem. Res. 25 (1982) 395 (f) Hayashi, T. and Kumada, M. In: Ishii, Y. and Tsutsui M., Eds.: Fundamental Research in Homogeneous Catalysis, Plenum, New York 1978, Vol. 2, p. 159.
16. (a) Hayashi, T., Kishi, K., Yamamoto, A. and Ito, Y. Tetrahedron Lett. 31 (1990) 1743
17. (b) Hayashi, T., Yamamoto, A., Ito, Y., Nishioka, E., Miura, H. and Yanagi, K. J. Am. Chem. Soc. 111 (1989) 6301
18. (c) Yamamoto, A., Ito, Y. and Hayashi, T. Tetrahedron Lett. 30 (1989) 375
19. (d) Hayashi, T., Kanehira, K., Hagihara, T. and Kumada, M. J. Org. Chem. 53 (1988) 113
20. (e) Hayashi, T., Yamamoto, A. and Ito, Y. Tetrahedron Lett. 29 (1988) 99
21. (f) Hayashi, T., Yamamoto, A. and Ito, Y. Chem. Lett. (1987) 177
22. (g) Hayashi, T., Yamamoto, A., Hagihara, T. and Ito, Y. Tetrahedron Lett. 27 (1986) 191.
23. (a) Hayashi, T., Sawamura, M. and Ito, Y. Tetrahedron 48 (1992) 1999
24. (b) Sawamura, M., Ito, Y. and Hayashi, T. Tetrahedron Lett. 30 (1989) 2247
25. (c) Ito, Y., Sawamura, M. and Hayashi, T. Tetrahedron Lett. 29 (1988) 239
26. (d) Ito, Y., Sawamura, M., Shirakawa, E., Hayashizaki, K. and Hayashi, T. Tetrahedron Lett. 29 (1988) 235
27. (e) Ito, Y., Sawamura, M., Shirakawa, E., Hayashizaki, K. and Hayashi, T. Tetrahedron 44 (1988) 5253
28. (f) Ito, Y., Sawamura, M. and Hayashi, T. Tetrahedron Lett. 28 (1987) 6215
29. (g) Ito, Y., Sawamura, M. and Hayashi, T. J. Am. Chem. Soc. 108 (1986) 6405
30. (h) Hayashi, T., Uozumi, Y., Yamazaki, A., Sawamura, M., Hamashima, H. and Ito, Y. Tetrahedron Lett. 32 (1991) 2799.
31. Examples of optically active monophosphine ligands: (a) (S)-(o-Methoxyphenyl)-cyclohexylmethylphosphine [(S)-CAMP]: Knowles, W. S., Sabacky, M. J. and Vineyard, B. D. J. Chem. Soc., Chem. Commun. (1972) 10 (b) Neomenthyldiphenylphosphine: Morrison, J. D., Burnett, R. E., Aguiar, A. M., Morrow, C. J. and Phillips, C. J. Am. Chem. Soc. 93 (1971) 1301.
32. Examples of optically active monophosphine ligands: (a) (S)-(o-Methoxyphenyl)-cyclohexylmethylphosphine [(S)-CAMP]: Knowles, W. S., Sabacky, M. J. and Vineyard, B. D. J. Chem. Soc., Chem. Commun. (1972) 10 (b) Neomenthyldiphenylphosphine: Morrison, J. D., Burnett, R. E., Aguiar, A. M., Morrow, C. J. and Phillips, C. J. Am. Chem. Soc. 93 (1971) 1301.
33. Hayashi, T., Hayashizaki, K.,. Kiyoi, T. and Ito, Y. J. Am. Chem. Soc. 110 (1988) 8153.
34. Kurz, L., Lee, G., Morgans, D., Jr., Waldyke, M. J. and Ward, T. Tetrahedron Lett. 31 (1990) 6321.
35. Uozumi, Y. and Hayashi, T. J. Am. Chem. Soc. 123 (1991) 9887.
36. Uozumi, Y., Tanahashi, A., Lee, S.-Y. and Hayashi. T. J. Org. Chem. 58 (1993) 1945.
37. Uozumi, Y., Suzuki, N., Ogiwara, A. and Hayashi, T. Tetrahedron 50 (1994) 4293.
38. Hayashi, T., Iwamura, H., Uozumi, Y., Matsumoto, Y. and Ozawa, F. Synthesis (1994) 526.
39. Uozumi, Y., Kitayama, K., Hayashi, T., Yanagi, K. and Fukuyo, E. Bull. Chem. Soc. Jpn. 68 (1995) 713.
40. 2[(R)-BINAP] has been reported: Ozawa, F., Kubo, A., Matsumoto, Y., Hayashi, T., Nishioka, E., Yanagi, K. and Moriguchi, K. Organometallics 12 (1993) 4188.
41. Pelter, A., Smith. K. and Brown, H. C. Borane Reagents, Academic Press, New York 1988.
42. (a) Hayashi, T., Matsumoto, Y. and Ito, Y. Tetrahedron Asymmetry 2 (1991) 601 and references cited therein
43. (b) Burgess, K., van der Donk, W. A. and Ohlmeyer, M. J. Tetrahedron Asymmetry 2 (1991) 613.
44. (a) Hayashi, T., Tamao, K., Katsuro, Y., Nakae, I. and Kumada, M. Tetrahedron Lett. 21 (1980) 1871
45. (b) Hayashi, T. and Kabeta, K. Tetrahedron Lett. 26 (1985) 3023 and references cited therein.
46. For a review: Ojima, I. In: Patai, S. and Rappoport, Z., Eds., The Chemistry of Organic Silicon Compounds, Wiley, Chichester 1989, p. 1479.
47. Tsuji, J., Hara, M. and Ohno, K. Tetrahedron 30 (1974) 2143.
48. Uozumi, Y., Kitayama, K. and Hayashi, T. Unpublished results.
49. (a) Tamao, K., Ishida, N., Tanaka, T. and Kumada, M. Organometallics 2 (1983) 1694
50. (b) Tamao, K. and Ishida, N. J. Organomet. Chem. 269 (1984) C37
51. (c) Tamao. K., Nakajo, E. and Ito, Y. J. Org. Chem. 52 (1987) 4412
52. (d) Tamao, K. In: Sakurai, H., Ed., Organosilicon and Bioorganosilicon Chemistry, Ellis Horwood, Chichester 1985, p. 231.
53. For reviews: (a) Morrison, J. D., Ed. Asymmetric Synthesis, Academic Press, London, 1983-1985, Vol. 1-5 (b) Nógrádi, M. Stereoselective Synthesis, Weinheim, New York 1987.
54. For reviews: (a) Morrison, J. D., Ed. Asymmetric Synthesis, Academic Press, London, 1983-1985, Vol. 1-5 (b) Nógrádi, M. Stereoselective Synthesis, Weinheim, New York 1987.
55. Uozumi, Y., Lee, S.-Y. and Hayashi, T. Tetrahedron Lett. 33 (1992) 7185.
56. Tamao, K., Yoshida, J., Murata, M. and Kumada, M. J. Am. Chem. Soc. 102 (1980) 3267.
57. Uozumi, Y. and Hayashi, T. Tetrahedron Lett. 34 (1993) 2335.
58. Uozumi, Y., Kitayama, K. and Hayashi, T. Tetrahedron Asymmetry 4 (1993) 2419.
59. For the asymmetric hydrosilylation of styrene with other chiral ligands: (a) Yamamoto, K., Kiso, Y., Ito, R., Tamao, I. and Kumada, M. J. Organomet. Chem. 210 (1981) 9 (b) Okada, T., Morimoto, T. and Achiwa, K. Chem. Lett. (1990) 999 (c) Marinetti, A. Tetrahedron Lett. 35 (1994) 5861 (d) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956.
60. For the asymmetric hydrosilylation of styrene with other chiral ligands: (a) Yamamoto, K., Kiso, Y., Ito, R., Tamao, I. and Kumada, M. J. Organomet. Chem. 210 (1981) 9 (b) Okada, T., Morimoto, T. and Achiwa, K. Chem. Lett. (1990) 999 (c) Marinetti, A. Tetrahedron Lett. 35 (1994) 5861 (d) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956.
61. For the asymmetric hydrosilylation of styrene with other chiral ligands: (a) Yamamoto, K., Kiso, Y., Ito, R., Tamao, I. and Kumada, M. J. Organomet. Chem. 210 (1981) 9 (b) Okada, T., Morimoto, T. and Achiwa, K. Chem. Lett. (1990) 999 (c) Marinetti, A. Tetrahedron Lett. 35 (1994) 5861 (d) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956.
62. For the asymmetric hydrosilylation of styrene with other chiral ligands: (a) Yamamoto, K., Kiso, Y., Ito, R., Tamao, I. and Kumada, M. J. Organomet. Chem. 210 (1981) 9 (b) Okada, T., Morimoto, T. and Achiwa, K. Chem. Lett. (1990) 999 (c) Marinetti, A. Tetrahedron Lett. 35 (1994) 5861 (d) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956.
63. Kitayama, K., Uozumi Y. and Hayashi, T. J. Chem. Soc., Chem. Commun. (1995) 1533.
64. Kitayama, K., Uozumi, Y. and Hayashi, T. Unpublished results.
65. For the asymmetric hydrosilylation of 1,3-dienes with other chiral ligands: (a) Hayashi, T., Hengrasmee, S. and Matsumoto, Y. Chem. Lett. (1990) 1377, and references cited therein (b) Okada, T., Morimoto, T. and Achiwa, K. Chem Lett. (1990) 999 (c) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956 (d) Hatanaka, Y., Goda, K., Yamashita, F. and Hiyama, T. Tetrahedron Lett. 35 (1994) 7981.
66. For the asymmetric hydrosilylation of 1,3-dienes with other chiral ligands: (a) Hayashi, T., Hengrasmee, S. and Matsumoto, Y. Chem. Lett. (1990) 1377, and references cited therein (b) Okada, T., Morimoto, T. and Achiwa, K. Chem Lett. (1990) 999 (c) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956 (d) Hatanaka, Y., Goda, K., Yamashita, F. and Hiyama, T. Tetrahedron Lett. 35 (1994) 7981.
67. For the asymmetric hydrosilylation of 1,3-dienes with other chiral ligands: (a) Hayashi, T., Hengrasmee, S. and Matsumoto, Y. Chem. Lett. (1990) 1377, and references cited therein (b) Okada, T., Morimoto, T. and Achiwa, K. Chem Lett. (1990) 999 (c) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956 (d) Hatanaka, Y., Goda, K., Yamashita, F. and Hiyama, T. Tetrahedron Lett. 35 (1994) 7981.
68. For the asymmetric hydrosilylation of 1,3-dienes with other chiral ligands: (a) Hayashi, T., Hengrasmee, S. and Matsumoto, Y. Chem. Lett. (1990) 1377, and references cited therein (b) Okada, T., Morimoto, T. and Achiwa, K. Chem Lett. (1990) 999 (c) Marinetti, A. and Ricard, L. Organometallics 13 (1994) 3956 (d) Hatanaka, Y., Goda, K., Yamashita, F. and Hiyama, T. Tetrahedron Lett. 35 (1994) 7981.
69. Kobayashi, S. and Nishio, K. J. Org. Chem. 59 (1994) 6620.
70. Matsumoto, Y., Naito, M. and Hayashi, T. Organometallics 11 (1992) 2732.
71. Matsumoto, Y., Naito, M., Uozumi, Y. and Hayashi, T. J. Chem. Soc., Chem. Commun. (1993) 1468.
72. (a) Tsuji, I. and Yamakawa, T. Tetrahedron Lett. (1979) 613
73. (b) Tsiji, J., Shimizu, I. and Minami, I. Chem. Lett. (1984) 1017
74. (c) Tsuji, J., Minami, I. and Shimizu, I. Synthesis (1986) 623
75. (d) Mandai, T., Matsumoto, T., Kawada, M. and Tsuji, J. J Org. Chem. 57 (1992) 1326
76. (e) Oshima, M., Shimizu, I., Yamamoto, A. and Ozawa, F. Organometallics 10 (1991) 1221.
77. Hayashi, T, Iwamura, H., Naito, M., Matsumoto, Y., Uozumi, Y., Miki, M. and Yanagi, K. J Am. Chem. Soc. 116 (1994) 775.
78. Hayashi, T., Iwamura, H. and Uozumi, Y. Tetrahedron Lett. 35 (1994) 4813.