A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar: Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4471-4474

  Liu, Duan ^a   Li, Wenge ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; MANNITOL; PHOSPHINE DERIVATIVE; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGENATION; SYNTHESIS;

CATALYSIS; HYDROGENATION; LIGANDS; MANNITOL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHOSPHINES; RHODIUM;

EID: 0037069709     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0269998     Document Type: Article

References (23)

1. Stinson, S. C. Chem. Eng. News 2001, 79(20), 45.
2. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, New York, 1999; Vols. I-III. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994. (d) Sheldon, R. A. Chirotechnology; Marcel Dekker: New York, 1993.
3. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, New York, 1999; Vols. I-III. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994. (d) Sheldon, R. A. Chirotechnology; Marcel Dekker: New York, 1993.
4. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, New York, 1999; Vols. I-III. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994. (d) Sheldon, R. A. Chirotechnology; Marcel Dekker: New York, 1993.
5. For recent reviews, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000. (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, New York, 1999; Vols. I-III. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley-Interscience: New York, 1994. (d) Sheldon, R. A. Chirotechnology; Marcel Dekker: New York, 1993.
6. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
7. Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602.
8. Almena Perea, J. J.; Börner, A.; Knochel, P. Tetrahedron Lett. 1998, 39, 8073.
9. Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425.
10. (a) Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. J. Org. Chem. 1998, 63, 8031.
11. (b) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. Tetrahedron Lett. 1999, 40, 6701.
12. (c) Yan, Y.; RajanBabu, T. V. Org. Lett. 2000, 2, 199.
13. (d) Yan, Y.; RajanBabu, T. V. J. Org. Chem. 2000, 65, 900.
14. (e) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
15. (f) RajanBabu, T. V.; Yan, Y.; Shin, S. J. Am. Chem. Soc. 2001, 123, 10207.
16. Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363.
17. Marinetti, A.; Labrue, F.; Genet, J.-P. Synlett 1999, 12, 1975.
18. Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2000, 39, 1981.
19. A great activity enhancement was observed in Ru-catalyzed transfer hydrogenation of ketones by introducing a ketal functionality at the rear end of the ligand presumably due to remote dipole effects: Nordin, S. J. M.; Roth, P.; Tarnai, T.; Alonso, D. A.; Brandt, P.; Andersson, P. G. Chem. Eur. J. 2001, 7, 1431.
20. (a) Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523.
21. (b) Almena Perea, J. J.; Lotz, M.; Knochel, P. Tetrahedron: Asymmetry 1999, 10, 375.
22. (c) Nettekoven, U.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Widhalm, M.; Spek, A. L.; Lutz, M. J. Org. Chem. 1999, 64, 3996.
23. 2 pressure for 12 h following a similar procedure described in the experimental section. The reactions went with 100% conversion. The R absolute configuration was assigned by comparison of optical rotation with reported data. Enantiomeric excesses were determined on the corresponding dimethyl esters by chiral GC using a γ-225 column.