PH-regulated asymmetrie transfer hydrogénation of quinolines in water

Angewandte Chemie - International Edition

Volumn 48, Issue 35, 2009, Pages 6524-6528

  Wang, Chao ^a   Li, Chaoqun ^a   Wu, Xiaofeng ^a   Pettman, Alan ^b   Xiao, Jianliang ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b Global Research And   (United Kingdom)

Author keywords

Aqueous media; Asymmetric transfer hydrog nation; Ph effects; Quinolines; Rhodium

Indexed keywords

AQUEOUS MEDIA; ASYMMETRIC TRANSFER HYDROGENATION; HYDROGEN SOURCES; QUINOLINE DERIVATIVE; QUINOLINES; RHODIUM CATALYSTS;

ENANTIOSELECTIVITY; HYDROGEN; RHODIUM; SODIUM;

PH EFFECTS;

QUINOLINE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; HYDROGENATION; PH;

HYDROGEN-ION CONCENTRATION; HYDROGENATION; QUINOLINES; WATER;

EID: 70349902205     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902570     Document Type: Article

References (71)

1. A. R. Katritzky, S. Rachwal, B. Rachwal, Tetrahedron 1996, 52, 15031.
2. a) J. H. Rakotoson, N. Fabre, I. lacquemond-Collet, S. Hannedouche, I. Fourasté, C. Moulis, Planta Med. 1998, 64, 762;
3. b) I. lacquemond-Collet, S. Hannedouche, N. Fabre, I. Fourasté, C. Moulis, Phytochemistry 1999, 51, 1167.
4. P. J. Houghton, T.Z. Woldemariam, Y. Watanabe, M. Yates, Planta Med. 1999, 65, 250.
5. For examples of the asymmetric hydrogénation of quinolines, see: a) W B. Wang, S. M. Lu, P. Y. Yang, X. W. Han, Y. G.Zhou, J.Am. Chem. Soc. 2003, 125, 10536;
6. b) L. J. Xu, K. H. Lam, J. X. Ji, J.Wu, Q. H. Fan, W H. Lo, A. S. C. Chan, Chem. Commun. 2005, 1390;
7. c)M.T. Reetz, X. G. Li, Chem. Commun. 2006, 2159;
8. d) S. M. Lu, C. BoIm, Adv. Synth. Catal. 2008, 350, 1101;
9. e) N.Mršič, L. Lefort, J.A. F. Boogers, A. J. Minnaard, B. L. Feringa, J.G. de Vries, Adv. Synth. Catal. 2008, 350, 1081;
10. f) 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;
11. g) 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;
12. Angew. Chem. Int. Ed. 2008, 47, 8464;
13. h) D. W. Wang, X. B. Wang, D. S. Wang, S. M. Lu, Y. G. Zhou, Y. X. Li, J. Org. Chem. 2009, 74, 2780.
14. a) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem. 2006, 118, 3765;
15. Angew. Chem. Int. Ed. 2006, 45, 3683;
16. b) M. Rueping, T. Theissmann, S. Raja, J. W. Bats, Adv. Synth. Catal. 2008, 350, 1001;
17. c) Q. S. Guo, D. M. Du, J.Xu, Angew. Chem. 2008, 120, 771;
18. Angew. Chem. Int. Ed. 2008, 47, 759.
19. For reviews on ATH, see : a) R. Noyori, S. Hashiguchi, Ace. Chem. Res. 1997, 30, 97;
20. b) M. J. Palmer, M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045;
21. c) K. Everaere, A. Mortreux, J.F. Carpentier, Adv. Synth. Catal. 2003, 345, 67;
22. d) S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226;
23. e) S. E. Clapham, A. Hadzovic, R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201;
24. f) J. S. M. Samec, J.E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev. 2006, 35, 237;
25. g) X. F. Wu, J. L. Xiao, Chem. Commun. 2007, 2449;
26. h) T Ikariya, A. J. Blacker, Ace. Chem. Res. 2007, 40, 1300;
27. i) C. Wang, X. F. Wu, J. L. Xiao, Chem. Asian J.2008, 3, 1750.
28. For examples of the non-asymmetric transfer hydrogénation of quinolines, see:
29. a) K. Fujita, C. Kitatsuji, S. Furukawa, R. Yamaguchi, Tetrahedron Lett. 2004, 45, 3215;
30. b) A. M. Voutchkova, D. Gnanamgari, C. E. Iakobsche, C. Butler, S. J. Miller, J. Parr, R. H. Crabtree, J. Organomet. Chem. 2008, 693, 1815.
31. An iridium-catalyzed ATH of quinolines with the Hantzsch ester in toluene/dioxane was reported recently (10-87 % ee): D. W. Wang, W Zeng, Y. G. Zhou, Tetrahedron: Asymmetry 2007, 18, 1103.
32. For recent reviews on organic reactions in water, see : a) U. M. Lindström, Chem. Rev. 2002, 102, 2751;
33. b) S. Kobayashi, K. Manabe, Ace. Chem. Res. 2002, 35, 209;
34. c) C. J. Li, Chem. Rev. 2005, 105, 3095;
35. d)T. Dwars, E. Paetzold, G. Oehme, Angew. Chem. 2005, 117, 7338;
36. Angew. Chem. Int. Ed. 2005, 44, HlA;
37. e) A. Chanda, V. V. Fokin, Chem. Rev. 2009, 109, 725.
38. a) S. Narayan, J. Muldoon, M. G.Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. 2005, 117, 3339;
39. Angew. Chem. Int. Ed. 2005, 44, 3275;
40. b)X.F. Wu, J.K. Liu, X. H. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. W. Ruan, J. L. Xiao, Angew. Chem. 2006, 118, 6870;
41. Angew. Chem. Int. Ed. 2006, 45, 6718;
42. c) N.Mase, Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, C. F. Barbas III, J. Am. Chem. Soc. 2006, 128, 734.
43. a) X. F. Wu, X. G. Li, W Hems, F. King, J. L. Xiao, Org. Biomol. Chem. 2004, 2, 1818;
44. b) X. F. Wu, X. G.Li, F. King, J. L. Xiao, Angew. Chem. 2005, 117, 3473;
45. Angew. Chem. Int. Ed. 2005, 44, 3407;
46. c) X. F. Wu, X. H. Li, A. Zanotti-Gerosa, A. Pettman, J. K. Liu, A. J. Mills, J. L. Xiao, Chem. Eur. J. 2008, 14, 2209.
47. a) C. Bubert, J. Blacker, S. M. Brown, J. Crosby, S. Fitzjohn, J. P. Muxworthy, T. Thorpe, J. M. J. Williams, Tetrahedron Lett. 2001, 42, 4037;
48. b)H.Y.Rhyoo, H.J.. Park, Y.K. Chung, Chem. Commun. 2001, 2064;
49. c) P. N.Liu, J. G.Deng, Y.Q. Tu, S. H. Wang, Chem. Commun. 2004, 2070;
50. d) J. Canivet, G. Labat, H. Stoeckli-Evans, G.Süss-Fink, Eur. J. Inorg. Chem. 2005, 4493;
51. e) D. S. Matharu, D. J. Morris, G. J. Clarkson, M. Wills, Chem. Commun. 2006, 3232;
52. f) C. Letondor, A. Pordea, N. Humbert, A. Ivanova, S. Mazurek, M. Novic, T. R. Ward, J. Am. Chem. Soc. 2006, Í25, 8320;
53. g) D. M. Iiang, J. S. Gao, Q. H. Yang, J. Yang, C. Li, Chem. Mater. 2006, 18, 6012;
54. h) H. F. Zhou, Q. H. Fan, Y. Y. Huang, L. Wu, Y. M. He, W.J. Tang, L. Q. Gu, A. S. C. Chan, J. Mol. Catal. A 2007, 275, 47;
55. i) S. Itsuno, M. Takahashi, Y. Arakawa, N.Haraguchi, Pure Appl. Chem. 2007, 79, 1471;
56. j) A. Schlatter, W. D. Woggon, Adv. Synth. Catal. 2008, 350, 995;
57. k) K. Ahlford, J. Lind, L. Maler, H. Adolfsson, Green Chem. 2008, 10, 832.
58. For examples of the ATH of imines in water, see: a) J. S. Wu, F. Wang, Y. P. Ma, X. Cui, L. F. Cun, J. Zhu, J. G.Deng, B. L. Yu, Chem. Commun. 2006 ,1766;
59. b) J. Canivet, G.Süss-Fink, Green Chem. 2007, 9, 391.
60. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J.Am. Chem. Soc. 1995, 117, 1562.
61. K. Mashima, T Abe, K. Tani, Chem. Lett. 1998, 1199.
62. For examples of mechanistic studies of imine reduction, see:
63. a) D. G. Blackmond, M. Ropic, M. Stefinvic, Org. Process Res. Dev. 2006, 10, 457;
64. b) J. B. Àberg, J. S. M. Samec, J. E. Bäckvall, Chem. Commun. 2006, 2771;
65. c) C. P. Casey, T. B. Clark, I. A. Guzei, J.Am. Chem. Soc. 2007, 129, 11821;
66. d) J. E. D Martins, G. J. Clarkson, M. Wills, Org. Lett. 2009, 11, 847.
67. a) H. Guan, M. Iimura, M. P. Magee, J. R. Norton, G. Zhu, J.Am. Chem. Soc. 2005, 127, 7805;
68. b) T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C. Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724.
69. a) C. Q. Li, C. Wang, B. Villa-Marcos, J. L. Xiao, J. Am. Chem. Soc. 2008, 130, 14450;
70. b) C. Q. Li, B. Villa-Marcos, J. L. Xiao, J.Am. Chem. Soc. 2009, 131, 6967.
71. The buffer capacities of a 2M HCOOH/HCOONa solution and a 2M HOAc/NaOAc solution (pH5) are 0.21 and 1.07, respectively.