Highly enantioselective hydrogenation of N-unprotected indoles using (S)-C10-BridgePHOS as the chiral ligand

Tetrahedron

Volumn 69, Issue 33, 2013, Pages 6839-6844

  Li, Chao ^a   Chen, Jianzhong ^a   Fu, Guanghong ^a   Liu, Delong ^a   Liu, Yangang ^a   Zhang, Wanbin ^a  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

Author keywords

(S) C10 BridgePHOS; Chiral indoline; N Unprotected indole; Pd catalyzed enantioselective hydrogenation

Indexed keywords

INDOLE DERIVATIVE; LIGAND; PALLADIUM; SOLVENT;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; METHODOLOGY; PRESSURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; SOLVENT EFFECT; SUBSTITUTION REACTION; TEMPERATURE SENSITIVITY;

EID: 84879839869     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.06.016     Document Type: Article

References (94)

1. A. Miyashita, H. Yasuda, H. Takaya, K. Toriumi, T. Ito, and R. Noyori J. Am. Chem. Soc. 102 1980 7932 7934
2. R. Noyori, and H. Takaya Acc. Chem. Res. 23 1990 345 350
3. J.G. Strong Pharma Chem. 2 2003 20 22
4. M. Berthod, G. Mignani, G. Woodward, and M. Lemaire Chem. Rev. 105 2005 1801 1836
5. Y.-M. Li, M. Yan, and A.S.C. Chan A. Börner, Phosphorus Ligands in Asymmetric Catalysis 2008 Wiley-VCH Weinheim 284 306
6. N. Arshad, and C.O. Kappe Adv. Heterocycl. Chem. 99 2010 33 59
7. T. Ohkuma, and N. Kurono Q.-L. Zhou, Privileged Chiral Ligands and Catalysts 2011 Wiley-VCH Weinheim 1 53 and references therein
8. R. Schmid, M. Cereghetti, B. Heiser, P. Schönholzer, and H.J. Hansen Helv. Chim. Acta 71 1988 897 929
9. R. Schmid, E.A. Broger, M. Cereghetti, Y. Crameri, J. Foricehr, M. Lalonde, R.K. Muller, M. Scalone, G. Schoettel, and U. Zutter Pure Appl. Chem. 68 1996 131 138
10. H. Shimizu, I. Nagasaki, and T. Saito Tetrahedron 61 2005 5405 5432 and references therein
11. H. Shimizu, I. Nagasaki, and T. Saito A. Börner, Phosphorus Ligands in Asymmetric Catalysis Vol. 1 2008 Wiley-VCH Weinhem 207 260
12. T. Saito, T. Yokozawa, T. Ishizaki, T. Moroi, N. Sayo, T. Miura, and H. Kumobayashi Adv. Synth. Catal. 343 2001 264 267 and references therein
13. C.-C. Pai, C.-W. Lin, C.-C. Lin, C.-C. Chen, and A.S.C. Chan J. Am. Chem. Soc. 122 2000 11513 11514
14. Z. Zhang, H. Qian, J. Longmire, and X. Zhang J. Org. Chem. 65 2000 6223 6226
15. S. Wu, W. Wang, W. Tang, M. Lin, and X. Zhang Org. Lett. 4 2002 4495 4497
16. A. Lei, S. Wu, M. He, and X. Zhang J. Am. Chem. Soc. 126 2004 1626 1627
17. C.-J. Wang, X. Sun, and X. Zhang Angew. Chem., Int. Ed. 44 2005 4933 4935
18. M. Raghunath, and X. Zhang Tetrahedron Lett. 46 2005 8213 8216
19. C.-J. Wang, X. Sun, and X. Zhang Synlett 2006 1169 1172 and references therein
20. S. Duprat de Paule, S. Jeulin, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, and P. Dellis Tetrahedron Lett. 44 2003 823 826
21. S. Duprat de Paule, S. Jeulin, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, and P. Dellis Org. Process Res. Dev. 7 2003 399 406
22. S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, and P. Dellis Angew. Chem., Int. Ed. 43 2004 320 325
23. J. Wu, J.-X. Ji, and A.S.C. Chan Proc. Natl. Acad. Sci. U.S.A. 102 2005 3570 3575
24. L. Qiu, F.Y. Kwong, J. Wu, W.H. Lam, S. Chan, W.-Y. Yu, Y.-M. Li, R. Guo, Z. Zhou, and A.S.C. Chan J. Am. Chem. Soc. 128 2006 5955 5965
25. R. Shintani, K. Yashio, T. Nakamura, K. Okamoto, T. Shimada, and T. Hayashi J. Am. Chem. Soc. 128 2006 2772 2773 and references therein
26. F. Wang, Y.J. Zhang, H. Wei, J. Zhang, and W. Zhang Tetrahedron Lett. 48 2007 4083 4086
27. F. Wang, Y.J. Zhang, G. Yang, and W. Zhang Tetrahedron Lett. 48 2007 4179 4182
28. Y.J. Zhang, F. Wang, and W. Zhang J. Org. Chem. 72 2007 9208 9213
29. H. Wei, Y.J. Zhang, F. Wang, and W. Zhang Tetrahedron: Asymmetry 19 2008 482 488
30. H. Wei, Y.J. Zhang, Y. Dai, J. Zhang, and W. Zhang Tetrahedron Lett. 49 2008 4106 4109
31. F. Wang, G. Yang, Y.J. Zhang, and W. Zhang Tetrahedron 64 2008 9413 9416
32. F. Fang, F. Xie, H. Yu, H. Zhang, B. Yang, and W. Zhang Tetrahedron 50 2009 6672 6675
33. Y.J. Zhang, H. Wei, and W. Zhang Tetrahedron 65 2009 1281 1286
34. F. Tian, D. Yao, Y.J. Zhang, and W. Zhang Tetrahedron 65 2009 9609 9615
35. H. Zhang, F. Fang, F. Xie, H. Yu, G. Yang, and W. Zhang Tetrahedron Lett. 51 2010 3119 3122
36. F. Fang, H. Zhang, F. Xie, G. Yang, and W. Zhang Tetrahedron 66 2010 3593 3598
37. F. Tian, D. Yao, Y. Liu, F. Xie, and W. Zhang Adv. Synth. Catal. 352 2010 1841 1845
38. B. Yang, F. Xie, H. Yu, K. Shen, Z. Ma, and W. Zhang Tetrahedron 67 2011 6197 6201
39. Q. Liu, K. Wen, Z. Zhang, Z. Wu, Y.J. Zhang, and W. Zhang Tetrahedron 68 2012 5209 5215
40. H. Yu, F. Xie, Z. Ma, Y. Liu, and W. Zhang Adv. Synth. Catal. 68 2012 1941 1947
41. H. Yu, F. Xie, Z. Ma, Y. Liu, and W. Zhang Org. Biomol. Chem. 10 2012 5137 5142
42. Y. Liu, and W. Zhang Angew. Chem., Int. Ed. 52 2013 2203 2206
43. C. Wang, G. Yang, J. Zhuang, and W. Zhang Tetrahedron Lett. 51 2010 2044 2047
44. I.W. Southon, and J. Buckingham Dictionary of Alkaloids 1989 Chapman and Hall New York, NY
45. N. Neuss A. Brossi, M. Suffness, The Alkaloids 1990 Academic Press San Diego 229
46. F. Gueritte, and J. Fahy G.M. Cragg, D.G.I. Kingstom, D.J. Newman, Anti-cancer Agents from Natural Products 2005 CRC Press Boca Raton 123
47. E. Fattorusso, and O. Taglialatela-Scafati Modern Alkaloids 2008 Wiley-VCH Weinheim and references therein
48. B. Orsat, P.B. Alper, W. Moree, C.-P. Mak, and C.-H. Wong J. Am. Chem. Soc. 118 1996 712 713
49. M. Keith, J.F. Larrow, and E.N. Jacobsen Adv. Synth. Catal. 343 2001 5 26
50. V.P. Krasnov, G.L. Levit, L.M. Bukrina, I.N. Andreeva, L.S. Sadretdinova, M.A. Korolyova, M.I. Kodess, V.N. Charushin, and O.N. Chupakhin Tetrahedron: Asymmetry 14 2003 1985 1988
51. F.O. Arp, and G.C. Fu J. Am. Chem. Soc. 128 2006 14264 14265
52. X.-L. Hou, and B.-H. Zheng Org. Lett. 11 2009 1789 1791
53. R. Viswanathan, E.N. Prabhakaran, M.A. Plotkin, and J.N. Johnston J. Am. Chem. Soc. 125 2003 163 168
54. K.T. Yip, M. Yang, K.L. Law, N.Y. Zhu, and D. Yang J. Am. Chem. Soc. 128 2006 3130 3131
55. I. Aillaud, J. Collin, C. Duhayon, R. Guillot, D. Lyubov, E. Schulz, and A. Trifonov Chem. - Eur. J. 14 2008 2189 2200
56. P.H. Fuller, J.-W. Kim, and S.R. Chemler J. Am. Chem. Soc. 130 2008 17638 17639
57. H. Yamamoto, E. Ho, I. Sasaki, M. Mitsutake, Y. Takagi, H. Imagawa, and M. Nishizawa Eur. J. Org. Chem. 2011 2417 2420
58. M. Nakanishi, D. Katayev, C. Besnard, and E.P. Kündig Angew. Chem., Int. Ed. 50 2011 7438 7441
59. J. Feltenberger, and R. Hsung Org. Lett. 13 2011 3114 3117
60. E.E. Maciver, S. Thompson, and M.D. Smith Angew. Chem., Int. Ed. 48 2009 9979 9982
61. M. Kimura, M. Futamata, R. Mukai, and Y. Tamaru J. Am. Chem. Soc. 127 2005 4592 4593
62. B.M. Trost, and J. Quancard J. Am. Chem. Soc. 128 2006 6314 6315
63. K.M.B. Gross, Y.M. Jun, and P. Beak J. Org. Chem. 62 1997 7679 7689
64. H.J.C. Deboves, C. Hunter, and R.F.W. Jackson J. Chem. Soc., Perkin Trans. 1 2002 733 736
65. A. Minatti, and S. Buchwald Org. Lett. 10 2008 2721 2724
66. J. Ruano, J. Alemán, S. Catalán, V. Marcos, S. Monteagudo, A. Parra, C. del Pozo, and S. Fustero Angew. Chem., Int. Ed. 47 2008 7941 7944
67. J.J. Li, T.S. Mei, and J.Q. Yu Angew. Chem., Int. Ed. 47 2008 6452 6455
68. D.B. Guthrie, and D.P. Curran Org. Lett. 11 2009 249 251
69. A. Bruch, R. Fröhlich, S. Grimme, A. Studer, and D.P. Curran J. Am. Chem. Soc. 133 2011 16270 16276
70. G. Sirasani, and R.B. Andrade Org. Lett. 13 2011 4736 4737
71. S. Anas, and H.B. Kagan Tetrahedron: Asymmetry 20 2009 2193 2199 and references therein
72. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029 3069
73. X. Cui, and K. Burgess Chem. Rev. 105 2005 3272 3296
74. S.-M. Lu, X.-W. Han, and Y.-G. Zhou Chin. J. Org. Chem. 25 2005 634 640
75. Y.-G. Zhou Acc. Chem. Res. 40 2007 1357 1366
76. J.-H. Xie, S.-F. Zhu, and Q.-L. Zhou Chem. Rev. 111 2010 1713 1760
77. D.-S. Wang, Q.-A. Chen, S.-M. Lu, and Y.-G. Zhou Chem. Rev. 112 2012 2557 2590
78. D.J. Ager, A.H.M. de Vries, and J.G. de Vries Chem. Soc. Rev. 41 2012 3340 3380
79. Q.-A. Chen, Z.-S. Ye, Y. Duan, and Y.-G. Zhou Chem. Soc. Rev. 42 2013 497 511 and references therein
80. R. Kuwano, K. Sato, T. Kurokawa, D. Karube, and Y. Ito J. Am. Chem. Soc. 122 2000 7614 7615
81. R. Kuwano, K. Kaneda, T. Ito, K. Sato, T. Kurokawa, and Y. Ito Org. Lett. 6 2004 2213 2215
82. R. Kuwano, and M. Kashiwabara Org. Lett. 8 2006 2653 2655
83. R. Kuwano, M. Kashiwabara, K. Sato, T. Ito, K. Kaneda, and Y. Ito Tetrahedron: Asymmetry 17 2006 521 535
84. N. Mršić, T. Jerphagnon, A.J. Minnaard, B.L. Feringa, and J.G. de Vries Tetrahedron: Asymmetry 21 2010 7 10
85. A. Baeza, and A. Pfaltz Chem. - Eur. J. 16 2010 2036 2039
86. A.M. Maj, I. Suisse, C. Méliet, and F. Agbossou-Niedercorn Tetrahedron: Asymmetry 21 2010 2010 2014
87. M. Rueping, C. Brinkmann, A. Antonchick, and I. Atodiresei Org. Lett. 12 2010 4604 4607
88. D.-S. Wang, Q.-A. Chen, W. Li, C.-B. Yu, Y.-G. Zhou, and X. Zhang J. Am. Chem. Soc. 132 2010 8909 8911
89. D.-S. Wang, J. Tang, Y.-G. Zhou, M.-W. Chen, C.-B. Yu, Y. Duan, and G.-F. Jiang Chem. Sci. 2 2011 803 806
90. Y. Duan, M.-W. Chen, Z.-S. Ye, D.-S. Wang, Q.-A. Chen, and Y.-G. Zhou Chem. - Eur. J. 17 2011 7193 7197
91. Y. Duan, M.-W. Chen, Q.-A. Chen, C.-B. Yu, and Y.-G. Zhou Org. Biomol. Chem. 10 2012 1235 1238
92. V. Gotor-Fernández, P. Fernández-Torres, and V. Gotor Tetrahedron: Asymmetry 17 2006 2558 2564
93. Y.-C. Xiao, C. Wang, Y. Yao, J. Sun, and Y.-C. Chen Angew. Chem., Int. Ed. 50 2011 10661 10664
94. A. Smith, and J.H.P. Utley Chem. Commun. 18 1965 427 428