Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis

Journal of Organic Chemistry

Volumn 70, Issue 5, 2005, Pages 1872-1880

  Boaz, Neil W ^a   Mackenzie, Elaine B ^a   Debenham, Sheryl D ^a   Large, Shannon E ^a   Ponasik Jr , James A ^a  

^a EASTMAN CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ESTERS; HYDROGENATION; NEGATIVE IONS; PHOSPHORUS; RHODIUM COMPOUNDS; STRUCTURE (COMPOSITION);

ACETYLFERROCENE; AMINOPHOSPHINES; ENANTIOSELECTIVITY; RHODIUM COMPLEXES;

SYNTHESIS (CHEMICAL);

ALPHA AMINO ACID; ESTER DERIVATIVE; FERROCENE DERIVATIVE; ITACONIC ACID; LIGAND; NITROGEN; PHOSPHINE DERIVATIVE; PHOSPHINOFERROCENYLAMINOPHOSPHINE; PHOSPHORUS; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; COMPLEX FORMATION; COST EFFECTIVENESS ANALYSIS; ENANTIOSELECTIVITY; HYDROGENATION; PROTEIN HYDROLYSIS; PROTEIN STABILITY; PROTEIN SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

AMINO ACIDS; CATALYSIS; ESTERS; FERROUS COMPOUNDS; HYDROGENATION; LIGANDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; RHODIUM; STEREOISOMERISM;

EID: 14544285465     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048312y     Document Type: Article

References (45)

1. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110. (b) Brown, J. M. in Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, pp 121-182. (c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069.
2. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110. (b) Brown, J. M. in Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, pp 121-182. (c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069.
3. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 1-110. (b) Brown, J. M. in Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, pp 121-182. (c) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069.
4. Fiorini, M.; Giongo, G. M. J. Mol. Catal. 1980, 7, 411 and references therein.
5. Reetz, M. T.; Neiberger, T.Angew. Chem., Int. Ed. 1999, 38, 179 and references therein.
6. (a) Cullen, W. R.; Sugi, Y. Tetrahedron Lett. 1978, 19, 1635.
7. (b) Selke, R.; Pracejus, H. J. Mol. Catal. 1986, 37, 213.
8. (c) Rajanbabu, T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
9. (d) Chan, A. S. C.; Hu, W.; Pai, C. C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 119, 9570.
10. Reetz, M. T.; Gosberg, A.; Goddard, R.; Kyung, S.-H. Chem. Commun. 1998, 2077 and references therein.
11. Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033.
12. (a) Krause, H. W.; Kruezfeld, H.-J.; Schmidt, U.; Dobler, Ch.; Michalik, M.; Taudien, S.; Fischer, C. H. Chirality 1996, 8, 173.
13. (b) Mi, A.; Lou, R.; Jiang, Y.; Deng, J.; Qin, Y.; Fu, F.; Li, Z.; Hu, W.; Chan, A. S. C. Synlett 1988, 847.
14. Reetz, M. T.; Gosberg, A. Tetrahedron: Asymmetry 1999, 10, 2129.
15. Francio, G.; Faraone, F.; Leitner, W. Angew. Chem., Int. Ed. 2000, 39, 1428.
16. Reetz, M. T.; Pasto, M. Tetrahedron Lett. 2000, 41, 3315.
17. A preliminary report of this work appeared in: Boaz, N. W.; Debenham, S. D.; Mackenzie, E. B.; Large, S. E. Org. Lett. 2002, 4, 2421-2424.
18. Münzenberg, R.; Rademacher, P.; Boese, R. J. Mol. Struct. 1998, 444, 77-90.
19. (a) Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389-5393.
20. (b) Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1072, 37, 3052-3058.
21. (a) Hayashi, T.; Mise, T.; Fukushima, M.; Kogatani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151.
22. (b) Yamamoto, K.; Wakatsuki, J.; Sugimoto, R. Bull. Chem. Soc. Jpn. 1980, 53, 1132-1137.
23. Togni, A.; Bruetel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066.
24. For reviews, see: (a) Richards, C. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. (b) Colcacot, T. J. Chem. Rev. 2003, 103, 3101-3118.
25. For reviews, see: (a) Richards, C. J. Tetrahedron: Asymmetry 1998, 9, 2377-2407. (b) Colcacot, T. J. Chem. Rev. 2003, 103, 3101-3118.
26. Gokel, G. W.; Ugi, I. K. J. Chem. Educ. 1972, 49, 294-296.
27. Boaz, N. W. Tetrahedron Lett. 1989, 30, 2061-2064.
28. (a) Wright, J.; Frambes, L.; Reeves, P. J. Organomet. Chem. 1994, 476, 215-217.
29. (b) Brieden, W. US Patent No. 5760264, 1998.
30. See, for example: Herbst, R. M.; Shemin, D. In Organic Synthesis; Blatt, A. H., Ed.; John Wiley: New York, 1943; Collect. Vol. 2; pp 1-3.
31. (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1984, 53-60.
32. (b) Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Synthesis 1992, 487-490.
33. (c) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172.
34. Kreuzfeld, H.-J.; Döbler, C.; Krause, H. W.; Facklam, C. Tetrahedron: Asymmetry 1993, 4, 2047-2051.
35. Reference 1a, pp 11-12.
36. See ref 1b, pp 124-132 and references therein.
37. Nogradi, M. In Stereoselective Synthesis; VCH: Weinheim, 1995; p 46 and references therein.
38. Oliver, J. D.; Riley, D. P. Organometallics 1983, 2, 1032-1038.
39. Armstrong, S. K.; Brown, J. M. Tetrahedron Lett. 1993, 34, 879-882.
40. Landis, C. R.; Halpern, J. J. Organomet. Chem. 1983, 250, 485-490.
41. Boaz, N. W.; Debenham, S. D.; Large, S. E.; Moore, M. K. Tetrahedron: Asymmetry 2003, 14, 3575-3580.
42. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. 1998, 37, 1931-1933.
43. Hayashi, T.; Hayashi, C.; Uozumi, Y. Tetrahedron: Asymmetry 1995, 6, 2503-2506.
44. (a) Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125.
45. (b) Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Winkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.