Catechol-based phosphoramidites: A new class of chiral ligands for rhodium-catalyzed asymmetric hydrogenations

Organic Letters

Volumn 6, Issue 9, 2004, Pages 1433-1436

  Hoen, Rob ^a   Van Den Berg, Michel ^a   Bernsmann, Heiko ^a   Minnaard, Adriaan J ^a   De Vries, Johannes G ^a   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CATECHOL; ENAMINE; HYDROGEN; LIGAND; PHOSPHORAMIDIC ACID DERIVATIVE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; HYDROGENATION;

EID: 2442480654     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049726g     Document Type: Article

References (49)

1. For reviews see: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. Homogeneous Hydrogenation; Kluwer: Dordrecht, 1994. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, Chapter 5.1. (c) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315.
2. For reviews see: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. Homogeneous Hydrogenation; Kluwer: Dordrecht, 1994. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, Chapter 5.1. (c) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315.
3. For reviews see: (a) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. Homogeneous Hydrogenation; Kluwer: Dordrecht, 1994. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 1, Chapter 5.1. (c) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315.
4. For a review, see: Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
5. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8515.
6. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
7. (a) Dang, T.-P.; Kagan, H. B. Chem. Commun. 1971, 481.
8. (b) Kagan, H. B.; Dang, T.-P. J. Am. Chem. Soc. 1972, 94, 6429.
9. (a) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
10. (b) Takaya, H.; Akutagawa, S.; Noyori, R. Org. Synth. 1988, 67, 20.
11. (a) Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100.
12. (b) Zhang, Z.; Zhy, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999, 64, 1774.
13. JosiPhos: Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. FerroPhos: Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523.
14. JosiPhos: Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062. FerroPhos: Kang, J.; Lee, J. H.; Ahn, S. H.; Choi, J. S. Tetrahedron Lett. 1998, 39, 5523.
15. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. Chem. Commun. 1972, 10.
16. (a) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, A. G.; Pringle, P. G. Chem. Commun. 2000, 961
17. (b) Reetz, M. T.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889
18. (c) Van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; Van Esch, J.; De Vries, A. H. M.; De Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.
19. (a) Komarov, I. V.; Börner, A. Angew. Chem., Int. Ed. 2001, 40, 1197.
20. (b) Reetz, M. T.; Mehler, G.; Meiswinkel, A.; Sell, T. Tetrahedron Lett. 2002, 43, 7941.
21. (c) Jia, X.; Li, X.; Xu, L.; Shi, Q.; Yao, X.; Chan, A. S. C. J. Org. Chem. 2003, 68, 4539.
22. (d) Reetz, M. T.; Sell, T.; Meiswinkel, A.; Mehler, G. Angew. Chem., Int. Ed. 2003, 42, 790.
23. (e) van den Berg, M.; Minnaard, A. J.; Haak, R. M.; Leeman, M.; Schudde, E. P.; Meetsma, A.; Feringa, B. L.; de Vries, A. H. M.; Maljaars, C. E. P.; Willans, C. E.; Hyett, D.; Boogers, J. A. F.; Henderickx, H. J. W.; de Vries, J. G. Adv. Synth. Catal. 2003, 345, 308.
24. (f) Li, X.; Jia, X.; Lu, G.; Au-Yeung, T. T.-L.; Lam, K.-H.; Lo, T. W. H.; Chan, A. S. C. Tetrahedron: Asymmetry 2003, 14, 2687.
25. (g) Jia, X.; Guo, R.; Li, X.; Yao, X.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 5541.
26. (h) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 2897.
27. (i) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977.
28. (j) Peña, D.; Minnaard, A. J.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 14552.
29. (k) Peña, D.; Minnaard, A. J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Org. Lett. 2003, 5, 475.
30. Doherty, S.; Robins, E. G.; Pál, I.; Newman, C. R.; Hardacre, C.; Rooney, D.; Mooney, D. A. Tetrahedron: Asymmetry 2003, 14, 1517.
31. (m) Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. J. Organomet. Chem. 2003, 675, 91.
32. (n) Reetz, M. T.; Mehler, G. Tetrahedron Lett. 2003, 44, 4593.
33. (o) Reetz, M. T.; Goossen, L. J.; Meiswinkel, A.; Paetzold, J.; Jensen, J. F. Org. Lett. 2003, 5, 3099.
34. (p) Peña, D.; Minnaard, A. J.; Boogers, J. A. F.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. Org. Biomol. Chem. 2003, 1, 1087.
35. (q) Ostermeier, M.; Brunner, B.; Korff, C.; Helmchen, G. Eur. J. Org. Chem. 2003, 3453.
36. (r) Van den Berg, M.; Haak, R. M.; Minnaard, A. J.; De Vries, A. H. M.; De Vries, J. G.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003.
37. MonoPhos (3) is commercially available from Strem chemicals.
38. (a) Chen, W.; Xiao, J. Tetrahedron Lett. 2001, 42, 8737.
39. (b) Fu, Y.; Xie, J.-H.; Hu, A.-G.; Zhou, H.; Wang, L.-X.; Zhou, Q.-L. Chem. Commun. 2002, 480.
40. (c) Hu, A.-G.; Fu Y.; Xie, J.-H.; Zhou, H. Wang, L-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2002, 41, 2348.
41. (d) Hannen, P.; Militzer, H.-C.; Vogl, E. M.; Rampf, F. A. Chem. Commun. 2003, 2210.
42. (e) Hua, Z.; Vassar, V. C.; Ojima, I. Org. Lett. 2003, 5, 3831.
43. Aldous, D. J.; Dutton, W. M.; Steel, P. G. Tetrahedron: Asymmetry 2000, 11, 2455.
44. 2 pressure.
45. (a) Lee, S.-g.; Zhang, Y. J. Org. Lett. 2002, 4, 2429
46. (b) Lubell, W. D.; Kitamura, M.; Noyori, R. Tetrahedron: Asymmetry 1991, 2, 543.
47. Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.
48. Gridnev, I. D.; Yasutake, M.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc. 2001, 123, 5268.
49. Reactions were run overnight, although in most cases reactions were completed in 4 h at 5 bar and in 2 h at 25 bar of hydrogen pressure.