Ruthenium-catalyzed asymmetric hydrogenation of N-Boc-indoles

Organic Letters

Volumn 8, Issue 12, 2006, Pages 2653-2655

  Kuwano, Ryoichi ^a   Kashiwabara, Manabu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745579608     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061039x     Document Type: Article

References (25)

1. (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029-3069.
2. (b) Blaser, H.-U.; Malan, C.; Pugin, B.; Spindler, F.; Steiner, H.; Studer, M. Adv. Synth. Catal. 2003, 345, 103-151.
3. (c) Kitamura, M.; Noyori, R. In Ruthenium in Organic Synthesis; Murahashi, S.-I., Ed.; Wiley-VCH: Weinheim, 2004; pp 3-52.
4. (d) Chi, Y.; Tang, W.; Zhang, X. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; pp 1-31.
5. Glorius, F. Org. Biomol. Chem. 2005, 3, 4171-4175.
6. (a) Bianchini, C.; Barbaro, P.; Scapacci, G.; Farnetti, E.; Graziani, M. Organometallics 1998, 17, 3308-3310.
7. (b) Henschke, J. P.; Burk, M. J.; Malan, C. G.; Herzberg, D.; Peterson, J. A.; Wildsmith, A. J.; Cobley, C. J.; Casy, G. Adv. Synth. Catal. 2003, 345, 300-307.
8. (a) Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125, 10536-10537.
9. (b) Yang, P.-Y.; Zhou, Y.-G. Tetrahedron: Asymmetry 2004, 15, 1145-1149.
10. (c) Lu, S.-M.; Han, X.-W.; Zhou, Y.-G. Adv. Synth. Catal. 2004, 346, 909-912.
11. (d) Lu, S.-M.; Wang, Y.-Q.; Han, X.-W.; Zhou, Y.-G. Angew. Chem., Int. Ed. 2006, 45, 2260-2263.
12. (e) Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q.-H.; Lo, W.-H.; Chan, A. S. C. Chem. Commun. 2005, 1390-1392.
13. (f) Lam, K. H.; Xu, L.; Feng, L.; Fan, Q.-H.; Lam, F. L.; Lo, W.-H.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1755-1758.
14. Legault, C. Y.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 8966-8967.
15. Glorius, F.; Spielkamp, N.; Holle, S.; Goddard, R.; Lehmann, C. W. Angew. Chem., Int. Ed. 2004, 43, 2850-2852.
16. (a) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614-7615.
17. (b) Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213-2215.
18. (e) Kuwano, R.; Kashiwabara, M.; Sato, K.; Ito, T.; Kaneda, K.; Ito, Y. Tetrahedron: Asymmetry 2006, 17, 521-535.
19. (a) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron: Asymmetry 1991, 2, 593-596.
20. (b) Sawamura, M.; Hamashima, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
21. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis. 3rd ed.; John Wiley & Sons: New York, 1999.
22. (a) Genêt, J. P.; Mallart, S.; Pinel, C.; Juge, S.; Laffitte, J. A. Tetrahedron: Asymmetry 1991, 2, 43-46.
23. (b) Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665-674.
24. Mashima, K.; Kusano, K.-H.; Sato, N.; Matsumura, Y.-I.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064-3076.
25. 6-arene ligand of 3. The arene ligand would be liberated from the ruthenium on starting the asymmetric hydrogenation; therefore, the geometry of PhTRAP would be kept trans during the reaction.