A new P-chiral bisphosphine, 1,1'-bis[(t- butyl)methylphosphino]ferrocene, as an effective ligand in catalytic asymmetric hydrosilylation of simple ketones

Tetrahedron Asymmetry

Volumn 10, Issue 5, 1999, Pages 877-882

  Tsuruta, Hideyuki ^a   Imamoto, Tsuneo ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE; KETONE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033548389     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00042-7     Document Type: Article

References (31)

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4. For recent examples, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271; (b) Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581; (c) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809; (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
5. For recent examples, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271; (b) Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581; (c) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809; (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
6. For recent examples, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271; (b) Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581; (c) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809; (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
7. For recent examples, see: (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271; (b) Brenchley, G.; Fedouloff, M.; Mahon, M. F.; Molloy, K. C.; Wills, M. Tetrahedron 1995, 51, 10581; (c) Brenchley, G.; Fedouloff, M.; Merifield, E.; Wills, M. Tetrahedron: Asymmetry 1996, 7, 2809; (d) Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
8. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
9. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
10. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
11. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
12. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
13. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
14. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
15. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
16. For representative examples of 1,1′-diphosphine substituted ferrocene ligands, see: (a) Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K.; Kumada, M. Tetrahedron Lett. 1976, 17, 1133; (b) Hayashi, T.; Kawamura, N.; Ito, Y. J. Am. Chem. Soc. 1987, 109, 7876; (c) Hayashi, T.; Yamamoto, A.; Ito, Y.; Nishioka, E.; Miura, H.; Yanag, K. J. Am. Chem. Soc. 1989, 111, 6302; (d) Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363; (e) Zhang, W.; Adachi, Y.; Hirano, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451; (f) Kaloun, E. B.; Merdès, R.; Genêt, J.-P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455; (g) Nettekoven, U.; Widhalm, M.; Kamer, P. C.; VanLeeuwen, P. W. N. M. Tetrahedron: Asymmetry 1997, 8, 3185; (h) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523; (i) Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S. H. Chem. Commun. 1998, 2077.
17. 1,1′-Diphosphine substituted ferrocene ligand has a large P-M-P bite angle at the transition metal complex, see: (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158; (b) Butler, I. R.; Cullen, W R.; Kim, T.-J.; Reltig, S. J.; Trotter, J. Organometallics 1985, 4, 972; (c) Hayashi, T.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Organomet. Chem. 1987, 334, 195.
18. 1,1′-Diphosphine substituted ferrocene ligand has a large P-M-P bite angle at the transition metal complex, see: (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158; (b) Butler, I. R.; Cullen, W R.; Kim, T.-J.; Reltig, S. J.; Trotter, J. Organometallics 1985, 4, 972; (c) Hayashi, T.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Organomet. Chem. 1987, 334, 195.
19. 1,1′-Diphosphine substituted ferrocene ligand has a large P-M-P bite angle at the transition metal complex, see: (a) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158; (b) Butler, I. R.; Cullen, W R.; Kim, T.-J.; Reltig, S. J.; Trotter, J. Organometallics 1985, 4, 972; (c) Hayashi, T.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Organomet. Chem. 1987, 334, 195.
20. (a) Imamoto, T. Pure Appl. Chem. 1993, 65, 655;
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22. For recent examples of rhodium-catalyzed asymmetric hydrosilylation of ketones, see: (a) Sudo, A.; Yoshida, H.; Saigo, K. Tetrahedron: Asymmetry 1997, 8, 3205; (b) Pastor, S. D.; Shum, S. P. Tetrahedron: Asymmetry 1998, 9, 543; (c) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics, 1998, 17, 398.
23. For recent examples of rhodium-catalyzed asymmetric hydrosilylation of ketones, see: (a) Sudo, A.; Yoshida, H.; Saigo, K. Tetrahedron: Asymmetry 1997, 8, 3205; (b) Pastor, S. D.; Shum, S. P. Tetrahedron: Asymmetry 1998, 9, 543; (c) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics, 1998, 17, 398.
24. For recent examples of rhodium-catalyzed asymmetric hydrosilylation of ketones, see: (a) Sudo, A.; Yoshida, H.; Saigo, K. Tetrahedron: Asymmetry 1997, 8, 3205; (b) Pastor, S. D.; Shum, S. P. Tetrahedron: Asymmetry 1998, 9, 543; (c) Haag, D.; Runsink, J.; Scharf, H.-D. Organometallics, 1998, 17, 398.
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