Transfer Hydrogenation with Ruthenium Complexes of Chiral (Phosphinoferrocenyl)oxazolines

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6104-6105

  Sammakia, Tarek ^a   Stangeland, Eric L ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001586112     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9711044     Document Type: Article

References (39)

1. Chowdhury, R. L.; Backvall, J.-E. J. Chem. Soc., Chem. Commun. 1991, 1063.
2. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
3. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
4. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
5. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
6. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
7. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
8. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
9. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
10. For a review, see: Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051. Gladiali, S.; Pinna, L.; Delogu, G.; DeMartin, S.; Zassinovich, G.; Mestroni, G. Tetrahedron: Asymmetry 1990, 1, 635. Muller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232. Krasik, P.; Alper, H. Tetrahedron 1994, 50, 4347. Yang, H.; Alvarez, M.; Lugan, N.; Mathieu, R. J. Chem. Soc. Chem. Commun. 1995, 1721. Langer, T.; Helmchen, G. Tetrahedron Lett. 1996, 37, 1381. Langer, T.; Janssen, J.; Helmchen, G. Tetrahedron: Asymmetry 1996, 7, 1599. Jiang, Q.; Van Plew, D.; Murtuza, S.; Zhang, X. Tetrahedron Lett. 1996, 37, 797. Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 215.
11. For other metal-based systems, see: Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800; Genet, J.-P.; Ratovelomanana-Vidal, V.; Pinel, C. Synlett, 1993, 478. Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. Varghese, J.; Iyers, S. J. Chem. Soc., Chem. Commun. 1995, 465;
12. For other metal-based systems, see: Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800; Genet, J.-P.; Ratovelomanana-Vidal, V.; Pinel, C. Synlett, 1993, 478. Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. Varghese, J.; Iyers, S. J. Chem. Soc., Chem. Commun. 1995, 465;
13. For other metal-based systems, see: Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800; Genet, J.-P.; Ratovelomanana-Vidal, V.; Pinel, C. Synlett, 1993, 478. Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. Varghese, J.; Iyers, S. J. Chem. Soc., Chem. Commun. 1995, 465;
14. For other metal-based systems, see: Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800; Genet, J.-P.; Ratovelomanana-Vidal, V.; Pinel, C. Synlett, 1993, 478. Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. Varghese, J.; Iyers, S. J. Chem. Soc., Chem. Commun. 1995, 465;
15. For other metal-based systems, see: Evans, D. A.; Nelson, S. G.; Gagné, M. R.; Muci, A. R. J. Am. Chem. Soc. 1993, 115, 9800; Genet, J.-P.; Ratovelomanana-Vidal, V.; Pinel, C. Synlett, 1993, 478. Gamez, P.; Fache, F.; Mangeney, P.; Lemaire, M. Tetrahedron Lett. 1993, 34, 6897. Gamez, P.; Fache, F.; Lemaire, M. Tetrahedron: Asymmetry 1995, 6, 705. Varghese, J.; Iyers, S. J. Chem. Soc., Chem. Commun. 1995, 465;
16. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. Haack, K. J.; Hashiguci, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. Hashiguci, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
17. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. Haack, K. J.; Hashiguci, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. Hashiguci, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
18. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97. Haack, K. J.; Hashiguci, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285. Hashiguci, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
19. (a) Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10;
20. (b) Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002.
21. (c) Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629.
22. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
23. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
24. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
25. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
26. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
27. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
28. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
29. For related work on the metalation of ferrocene oxazolines, see: Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3748. Park, J.; Lee, S.; Ahn, K. H.; Cho, C.-W. Tetrahedron Lett. 1995, 36, 7263. Richards, C. J.; Mulvaney, W. Tetrahedron: Asymmetry 1996, 7, 1419. Zhang, W.; Hirao, I.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545. Zhang, W.; Adachi, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 451. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
30. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron; Asymmetry 1996, 7, 1419. Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett, 1996, 37, 7995.
31. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron; Asymmetry 1996, 7, 1419. Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett, 1996, 37, 7995.
32. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron; Asymmetry 1996, 7, 1419. Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett, 1996, 37, 7995.
33. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron; Asymmetry 1996, 7, 1419. Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett, 1996, 37, 7995.
34. For examples of the use of related ligands in asymmetric catalysis, see: Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometallics 1995, 14, 5486. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545; Richards, C. J.; Mulvaney, A. W. Tetrahedron; Asymmetry 1996, 7, 1419. Zhang, W. B.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett, 1996, 37, 7995.
35. Berriaford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059.
36. 2O and 6 equiv triphenylphosphine in methanol for 3 h, during which time the product crystallizes (see: Stephenson, T. A.; Wilkinson, G. J. Inorg. Nucl. Chem, 1966, 28, 945).
37. Catalysts prepared using dichloro(1,5-cyclooctadiene)ruthenium(II) polymer or dichloro(p-cymene)ruthenium(II) dimer as catalyst precursors are also less reactive and unselective.
38. 3P (0.4%) and ligand 5 (0.4%) in i-PrOH for 1 h provides the expected (R)-carbinol in 90% ee and 76% conversion.
39. When tributylphosphine is substituted for triphenylphosphine, racemic material is produced at a greatly diminished rate.