Novel Ir-SYNPHOS® and Ir-DIFLUORPHOS® catalysts for asymmetric hydrogenation of quinolines

Synlett

Volumn , Issue 17, 2007, Pages 2743-2747

  Deport, Coralie ^a   Buchotte, Marie ^a   Abecassis, Keren ^a   Tadaoka, Hiroshi ^b   Ayad, Tahar ^a   Ohshima, Takashi ^b   Genet, Jean Pierre ^a   Mashima, Kazushi ^b   Ratovelomanana Vidal, Virginie ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Catalysts; Enantioselectivity; Hydrogenation; Iridium

Indexed keywords

IRIDIUM COMPLEX; QUINALDINE; QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; SYNTHESIS;

EID: 35649004432     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991076     Document Type: Article

References (42)

1. (a) Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031.
2. (b) See also Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
3. Witherup, K. M.; Ransom, R. W.; Varga, S. L.; Pitzenberger, S. M.; Lotti, V. J.; Lumma, V. J. US 5 288 725, 1994.
4. (a) Leeson, P. D.; Carling, R. W.; Moore, K. W.; Moseley, A. M.; Smith, J. D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A. C.; Grimwood, S.; Kemp, J. A.; Marshall, G. R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954.
5. (b) Yoneda, Y.; Suzuki, T.; Ogita, K.; Han, D. J. Neurochem. 1993, 60, 634.
6. (c) Mager, P. P. Drug Des. Discovery 1994, 11, 185.
7. Yang, P. Y.; Zhou, Y. G. Tetrahedron: Asymmetry 2004, 15, 1145.
8. Avemaria, F.; Vanderheiden, S.; Bräse, S. Tetrahedron 2003, 59, 6785.
9. (a) For a recent review, see: Glorius, F. Org. Biomol. Chem. 2005, 3, 4171; and references cited therein.
10. (b) Legault, C. Y.; Charette, A. B. J. Am. Chem. Soc. 2005, 127, 8966.
11. (c) Bianchini, C.; Barbara, P.; Scapacci, G.; Farnetti, E.; Graziani, M. Organometallics 1998, 17, 3308.
12. (d) 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.
13. (e) Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614.
14. (f) Kuwano, R.; Kaneda, K.; Ito, T.; Sato, K.; Kurokawa, T.; Ito, Y. Org. Lett. 2004, 6, 2213.
15. (a) Wang, W. B.; Lu, S. M.; Yang, P. Y.; Han, X. W.; Zhou, Y. G. J. Am. Chem. Soc. 2003, 125, 10536.
16. (b) Lu, S. M.; Han, X. W.; Zhou, Y. G. Adv. Synth. Catal. 2004, 346, 909.
17. (c) Lu, S.; Wang, Y.; Han, X. W.; Zhou, Y. G. Angew. Chem. Int. Ed. 2006, 45, 2260.
18. (a) Xu, L.; Lam, K. H.; Ji, J.; Wu, J.; Fan, Q. H.; Lo, W. H.; Chan, A. S. C. Chem. Commun. 2005, 1390.
19. (b) 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.
20. (c) Tang, W. J.; Zhu, S. F.; Xu, L. J.; Zhou, Q. L.; Fan, Q. H.; Zhou, H. F.; Lam, K.; Chan, A. S. C. Chem. Commun. 2007, 613.
21. (a) Reetz, M. T.; Li, X. Chem. Commun. 2006, 2159.
22. (b) Wang, Z. J.; Deng, G. J.; Li, Y.; He, Y. M.; Tang, W. J.; Fan, Q. H. Org. Lett. 2007, 9, 1243.
23. (a) Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. FR 2830254, 2001.
24. (b) Duprat de Paule, S.; Champion, N.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Dellis, P. WO 03029259, 2003.
25. (c) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Tetrahedron Lett. 2003, 44, 823.
26. (d) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Dellis, P. Eur. J. Org Chem. 2003, 1931.
27. (e) Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N.; Deschaux, G.; Dellis, P. Org. Process Res. Dev. 2003, 7, 399.
28. (a) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N. Angew. Chem. Int. Ed. 2004, 43, 320.
29. (b) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Champion, N. Proc Natl. Acad Sci. U.S.A. 2004, 101, 5799.
30. (a) Mordant, C.; Dünkelmann, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Chem. Commun. 2004, 1296.
31. (b) Mordant, C.; Dünkelmann, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Eur. J. Org Chem. 2004, 3017.
32. (c) Mordant, C.; Reymond, S.; Tone, H.; Lavergne, D.; Touati, R.; Ben Hassine, B.; Ratovelomanana-Vidal, V.; Genet, J.-P. Tetrahedron 2007, 343, 1592.
33. (d) Jeulin, S.; Ayad, T.; Ratovelomanana-Vidal, V.; Genet, J.-P. Adv. Synth. Catal. 2007, 63, 6115.
34. (a) Noyori, R. In Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994, 16.
35. (b) Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008.
36. (c) Ratovelomanana-Vidal, V.; Genet, J. P. J. Organomet. Chem. 1998, 567, 163.
37. (d) Ratovelomanana-Vidal, V.; Genet, J.-P. Can. J. Chem. 2000, 78, 846.
38. (e) Genet, J.-P. Acc. Chem. Res. 2003, 36, 908.
39. (a) Yamagata, T.; Tadaoka, H.; Nagata, M.; Hirao, T.; Kataoka, Y.; Ratovelomanana-Vidal, V.; Genet, J.-P.; Mashima, K. Organometallics 2006, 25, 2505.
40. See also: (b) Mashima, K.; Nakamura, T.; Matsuo, Y.; Tani, K. J. Organomet. Chem. 2000, 607, 51.
41. (c) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
42. 2 (50 bar) at 30°C for 24 h. After releasing the hydrogen, the reaction mixture was concentrated and the crude product was purified by a short silica gel column eluted with cyclohexane-EtOAc.