Unprecedented halide dependence on catalytic asymmetric hydrogenation of 2-aryl- and 2-alkyl-substituted quinolinium salts by using ir complexes with difluorphos and halide ligands

Chemistry - A European Journal

Volumn 15, Issue 39, 2009, Pages 9990-9994

  Tadaoka, Hiroshi ^a   Cartigny, Damien ^b   Nagano, Takuto ^a   Gosavi, Tushar ^b   Ayad, Tahar ^b   Genêt, Jean Pierre ^b   Ohshima, Takashi ^a   Ratovelomanana Vidal, Virginie ^b   Mashima, Kazushi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

Asymmetric synthesis; Enantioselectivity; Hydrogenation; Iridium; Quinolines

Indexed keywords

ASYMMETRIC HYDROGENATION; ASYMMETRIC SYNTHESIS; CATALYST PRECURSORS; CATALYST SYSTEM; CRUDE PRODUCTS; DINUCLEAR IRIDIUMS; DIPHOSPHINE LIGAND; ENANTIOSELECTIVE HYDROGENATION; ENVIRONMENTALLY BENIGN PROCESS; HALIDE COMPLEXES; HALIDE LIGAND; IR COMPLEXES; IRIDIUM CATALYST; NMR SPECTROSCOPIC ANALYSIS; QUINOLINES; TRANSITION-METAL COMPLEX;

CATALYSIS; CATALYSTS; COMPLEXATION; DYES; ELECTRON TRANSITIONS; ENANTIOSELECTIVITY; HYDROGENATION; IRIDIUM; LIGANDS; ORGANIC COMPOUNDS; SALTS; SPECTROSCOPIC ANALYSIS;

IRIDIUM COMPOUNDS;

EID: 70349653339     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901477     Document Type: Article

References (87)

1. For comprehensive reviews on asymmetric catalysis, see: a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994, Chapter 2, pp. 16-94;
2. b) J. M. Brown, R. L. Halterman, T. Ohkuma, R. Noyori, H.-U. Blaser, F. Spindler in Comprehensive Asymmetric Catalysis, Vol.1 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 122-266;
3. c) T. Ohkuma, M. Kitamura, R. Noyori in Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley-VCH, Weinheim, 2000, Chapter 1, pp. 1-110;
4. d) R. Noyori, H. Takaya, Acc. Chem. Res. 1990, 23, 345-350;
5. e) R. Noyori, T. Ohkuma, Angew. Chem. 2001, 113, 40-75;
6. Angew. Chem. Int. Ed. 2001, 40, 40-73;
7. f) R. Noyori, Angew. Chem. 2002, 114, 2108-2123;
8. Angew. Chem. Int. Ed. 2002, 41, 2008-2022;
9. g) J.-P. Genet, Acc. Chem. Res. 2003, 36, 908-918.
10. a) R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc. 1987, 109, 5856-5858;
11. b) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2675-2676;
12. c) H. Doucet, T. Ohkuma, K. Murata, T. Yokozawa, M. Kozawa, E. Katayama, A. F. England, T. Ikariya, R. Noyori, Angew. Chem. 1998, 110, 1792-1796;
13. Angew. Chem. Int. Ed. 1998, 37, 1703-1707;
14. d) K. Makino, T. Goto, Y. Hiroki, Y. Hamada, Angew. Chem. 2004, 116, 900-902;
15. Angew. Chem. Int. Ed. 2004, 43, 882-884;
16. e) T. Ohkuma, C. A. Sandoval, R. Srinivasan, Q. Lin, Y. Wei, K. Muniz, R. Noyori, J. Am. Chem. Soc. 2005, 127, 8288-8289;
17. f) T. Ohkuma, K. Tsutsumi, N. Utsumi, N. Arai, R. Noyori, K. Murata, Org. Lett. 2007, 9, 255-257;
18. g) T. Ohkuma, N. Utsumi, M. Watanabe, K. Tsutsumi, N. Arai, K. Murata, Org. Lett. 2007, 9, 2565-2567.
19. a) V. Ratovelomanana-Vidal, J.-P. Genet, Can. J. Chem. 2000, 78, 846-851;
20. b) J.-P. Genet, Pure Appl. Chem. 2002, 74, 77-83;
21. c) C. Mordant, P. Dünkelmann, V. Ratovelomanana-Vidal, J.-P. Genet, Chem. Commun. 2004, 1296-1297;
22. d) C. Mordant, S. Reymond, H. Tone, D. Lavergne, R. Touati, B. Ben Hassine, V. Ratovelomanana-Vidal, J.-P. Genet, Tetrahedron 2007, 63, 6115-6123.
23. a) A. Tritonova, J. S. Diesen, C. J. Chapman, P. G. Andersson, Org. Lett. 2004, 6, 3825-3827;
24. b) C. Moessner, C. Bolm, Angew. Chem. 2005, 117, 7736-7739;
25. Angew. Chem. Int. Ed. 2005, 44, 7564-7567;
26. c) Q. Yang, G. Shang, W. Gao, J. Deng, X. Zhang, Angew. Chem. 2006, 118, 3916-3919;
27. Angew. Chem. Int. Ed. 2006, 45, 3832-3835;
28. d) C. Li, J. Xiao, J. Am. Chem. Soc. 2008, 130, 13208-13209;
29. e) S. Shirai, H. Nara, Y. Kayaki, T. Ikariya, Organometallics 2009, 28, 802-809.
30. For the effects of iodide sources or iodine on Ir-catalyzed hydrogenation of imines, see: a) F. Spindler, B. Pugin, H.-U. Blaser, Angew. Chem. 1990, 102, 561-562;
31. Angew. Chem. Int. Ed. Engl. 1990, 29, 558-559;
32. b) F. Spindler, B. Pugin, H.-P. Jalett, H.-P. Buser, U. Pittelkow, H.-U. Blaser, Chem. Ind. 1996, 68, 153-166;
33. c) K. Satoh, M. Inenaga, K. Kanai, Tetrahedron: Asymmetry 1998, 9, 2657;
34. d) H.-U. Blaser, H.-P. Buser, K. Coers, R. Hanreich, H.-P. Jalett, E. Jelsch, B. Pugin, H.-D. Schneider, F. Spindler, A. Wegmann, Chimia 1999, 53, 275-280;
35. e) D. Xiao, X. Zhang, Angew. Chem. 2001, 113, 3533-3536;
36. Angew. Chem. Int. Ed. 2001, 40, 3425-3428;
37. f) R. Dorta, D. Broggini, R Stoop, H. Ruegger, F. Spindler, A. Togni, Chem. Eur. J. 2004, 10, 267-278.
38. T. Yamagata, H. Tadaoka, M. Nagata, T. Hirao, Y. Kataoka, V. Ratovelomanana-Vidal, J.-P. Genêt, K. Mashima, Organometallics 2006, 25, 2505-2513.
39. For recent reviews on hydrogenation of heteroaromatic compounds, see a) F. Glorius, Org. Biomol. Chem. 2005, 3, 4171-4175;
40. b) R. Kuwano, Heterocycles 2008, 76, 909-922.
41. For recent examples of asymmetric hydrogenation of heteroaromatic compounds other than quinolines, see a) R. Kuwano, K. Sato, T. Kurokawa, D. Karube, Y. Ito, J. Am. Chem. Soc. 2000, 122, 7614-7615;
42. b) C. Y. Legault, A. B. Charette, J. Am. Chem. Soc. 2005, 127, 8966-8967;
43. c) S. Kaiser, S. P. Smidt, A. Pfaltz, Angew. Chem. 2006, 118, 5318-5321;
44. Angew. Chem. Int. Ed. 2006, 45, 5194-5197;
45. d) M. Rueping, A. P. Antonchick, Angew. Chem. 2007, 119, 4646-4649;
46. Angew. Chem. Int. Ed. 2007, 46, 4562-4565;
47. e) R. Kuwano, M. Kashiwabara, M. Ohsumi, H. Kusano, J. Am. Chem. Soc. 2008, 130, 808-809.
48. a) W.-B. Wang, S.-M. Lu, P.-Y. Yang, X.-W. Han, Y-G. Zhou, J. Am. Chem. Soc. 2003, 125, 10536-10537;
49. b) S.-M. Lu, X.-W. Han, Y.-G. Zhou, Adv. Synth. Catal. 2004, 346, 909-912;
50. c) Y-G. Zhou, Acc. Chem. Res. 2007, 40, 1357-1366;
51. d) X.-B. Wang, Y-G. Zhou, J. Org. Chem. 2008, 73, 5640-5642;
52. e) X.-B. Wang, W. Zeng, Y-G. Zhou, Tetrahedron Lett. 2008, 49, 4922-4924;
53. f) D-W. Wang, X.-B. Wang, D.-S. Wang, S.-M. Lu, Y-G. Zhou, Y-X. Li, J. Org. Chem. 2009, 74, 2780-2787.
54. a) L. Xu, K. H. Lam, J. Ji, J. Wu, Q.-H. Fan, W.-H. Lo, A. S. C. Chan, Chem. Commun. 2005, 1390-1392;
55. b) K. H. Lam, L. Xu, L. Feng, Q.-H. Fan, F. L. Lam, W. Lo, A. S. C. Chan, Adv. Synth. Catal. 2005, 347, 1755-1758;
56. c) W.-J. Tang, S.-F. Zhu, L.-J. Xu, Q.-L. Zhou, Q.-H. Fan, H.-F. Zhou, K. Lam, A. S. C. Chan, Chem. Commun. 2007, 613-615;
57. d) S. H. Chan, K. H. Lam, Y-M. Li, L. Xu, W. Tang, F. L. Lam, W. H. Lo, W. Y. Yu, Q. Fan, A. S. C. Chan, Tetrahedron: Asymmetry 2007, 18, 2625-2631;
58. e) H. Zhou, Z. Li, Z. Wang, T. Wang, L. Xu, Y. He, Q.-H. Fan, J. Pan, L. Gu, A. S. C. Chan, Angew. Chem. 2008, 120, 8592-8595;
59. Angew. Chem. Int. Ed. 2008, 47, 8464-8467.
60. M. T. Reetz, X. Li, Chem. Commun. 2006, 2159-2160.
61. M. Jahjah, M. Alame, S. Pellet-Rostaing, M. Lemaire, Tetrahedron: Asymmetry 2007, 18, 2305-2312.
62. Z.-J. Wang, G.-J. Deng, Y. Li, Y-M. He, W.-J. Tang, Q.-H. Fan, Org. Lett. 2007, 9, 1243-1246.
63. N Mrsic, L. Lefort, J. A. F. Boogers, A. J. Minnaard, B. L. Feringa, J. G. de Vriesa, Adv. Synth. Catal. 2008, 350, 1081-1089.
64. S.-M. Lua, C. Bolm, Adv. Synth. Catal. 2008, 350, 1101-1105.
65. Z.-W. Li, T-L. Wang, Y-M. He, Z.-J. Wang, Q.-H. Fan, J. Pan, L.-J. Xu, Org. Lett. 2008, 10, 5265-5268.
66. C. Deport, M. Buchotte, K. Abecassis, H. Tadaoka, T. Ayad, T. Ohshima, J.-P. Genêt, K. Mashima, V. Ratovelomanana-Vidal, Synlett 2007, 2743-2747.
67. S.-M. Lu, Y-Q. Wang, X.-W. Han, Y-G. Zhou, Angew. Chem. 2006, 118, 2318-2321;
68. Angew. Chem. Int. Ed. 2006, 45, 2260-2263.
69. a) P. D. Leeson, R. W Carling, K. W. Moore, A M. Moseley, J D. Smith, G. Stevenson, T. Chan, R. Baker, A. C. Foster, Med. Chem. 1992, 35, 1954-1968;
70. b) Y. Yoneda, T. Suzuki, K. Ogita, D. Han, J. Neurochem. 1993, 60, 634-645;
71. c) P. P. Mager, Drug Des. Discovery 1994, 11, 185-196;
72. d) P. Y. Yang, Y. G. Zhou, Tetrahedron: Asymmetry 2004, 15, 1145-1149.
73. a) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N Champion, Angew. Chem. 2004, 116, 324-329;
74. Angew. Chem. Int. Ed. 2004, 43, 320-325;
75. b) S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N Champion, Proc. Natl. Acad. Sci. USA 2004, 101, 5799-5804.
76. The biological activity of a racemic form of 1 as a SERM have been examined, see :O. B. Wallace, K. S. Lauwers, S. A. Jones, J. A. Dodge, Bioorg. Med. Chem. Lett. 2003, 13, 1907-1910.
77. 2 (5 mL) was stirred for 3 h at RT. Upon addition of HX (10 equiv; X = Cl, Br, or I), the color of the solution immediately turned yellow. After stirring for an additional 30 min, all volatiles were removed under reduced pressure. The residue was washed three times with hexane to remove excess diphosphine ligand and cyclooctene. The obtained air-stable pale yellow complex was used for the hydrogenation without further purification.
78. See the Supporting Information for details.
79. a) X. Zhang, K. Mashima, K. Koyano, N. Sayo, H. Kumobayashi, S. Akutagawa, H. Takaya, J. Chem. Soc. Perkin Trans. 1 1994, 2309-2322;
80. b) T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, H. Kumobayashi, Adv. Synth. Catal. 2001, 343, 264-267;
81. c) S. Subongkoj, S. Lange, W. Chen, J. Xiao, J. Mol. Catal. A 2003, 196, 125-129.
82. For references regarding the asymmetric transfer hydrogenation of ketones, see : a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102;
83. b) T. Ikariya, A.J. Blacker, Acc. Chem. Res. 2007, 40, 1300-1308;
84. c) M. Kitamura, M. Yoshimura, N. Kanda, R. Noyori, Tetrahedron 1999, 55, 8769-8785;
85. d) R. Noyori, M. Kitamura, T. Ohkuma, Proc. Natl. Acad. Sci. USA 2004, 101, 5356-5362.
86. X. Zhang, T. Taketomi, T. Yoshizumi, H. Kumobayashi, S. Akutagawa, K. Mashima, H. Takaya, J. Am. Chem. Soc. 1993, 115, 3318-3319.
87. During the review process of our manuscript, W. Leitner et al. reported the asymmetric hydrogenation of 2-phenylquinoline using a phosphine- phosphoramidite with ee up to 95% and 72% conversion, see M. Eggenstein, A. Thomas, J. Theuerkauf, G. Franciò, W. Leitner, Adv. Synth. Catal. 2009, 351, 725-732.