Atom-economic, regiodivergent, and stereoselective coupling of imidazole derivatives with terminal allenes

Angewandte Chemie - International Edition

Volumn 53, Issue 8, 2014, Pages 2162-2165

  Xu, Kun ^a   Thieme, Niels ^a   Breit, Bernhard ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

allenes; allylic compounds; asymmetric catalysis; heterocycles; rhodium

Indexed keywords

ALLENES; ALLYLIC COMPOUNDS; ASYMMETRIC CATALYSIS; ENANTIOMERIC EXCESS; HETEROCYCLES; IMIDAZOLE DERIVATIVES; INTERMOLECULAR COUPLING; STEREO-SELECTIVE;

CATALYSIS; HYDROCARBONS; RHODIUM; STEREOSELECTIVITY;

RHODIUM COMPOUNDS;

ALKENE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; PALLADIUM; RHODIUM;

CATALYSIS; CHEMISTRY; STEREOISOMERISM;

ALKENES; CATALYSIS; IMIDAZOLES; PALLADIUM; RHODIUM; STEREOISOMERISM;

EID: 84893838746     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201309126     Document Type: Article

References (87)

1. J. A. Joule, K. Mills, Heterocyclic Chemistry, Wiley, Chichester, 2010, chap. 32-33
2. A. F. Pozharskii, A. T. Soldatenkov, A. R. Katritzky, Heterocycles in Life and Society, Wiley, Chichester, 2011, chap. 10
3. L. Yet, V. A. Ostrovskii, G. I. Koldobskii, R. E. Trifonow, in Comprehensive Heterocyclic Chemistry III, Vol.4 and 6 (Eds.:, A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor,), Elsevier Science & Technology, Oxford, 2008, pp. 112-121 and 393-407
4. T. Terasaka, T. Kinoshita, M. Kuno, N. Seki, K. Tanaka, I. Nakanishi, J. Med. Chem. 2004, 47, 3730-3743
5. Y. Xiang, Z. Hou, Z. Zhang, Chem. Biol. Drug Des. 2012, 79, 760-770.
6. B. M. Trost, Z. Shi, J. Am. Chem. Soc. 1996, 118, 3037-3038
7. B. M. Trost, R. Madsen, S. G. Guile, A. E. H. Elia, Angew. Chem. 1996, 108, 1666-1668
8. Angew. Chem. Int. Ed. Engl. 1996, 35, 1569-1572
9. B. M. Trost, R. Madsen, S. D. Guile, B. Brown, J. Am. Chem. Soc. 2000, 122, 5947-5956
10. B. M. Trost, G. Dong, J. Am. Chem. Soc. 2006, 128, 6054-6055
11. P. Dübon, M. Schelwies, G. Helmchen, Chem. Eur. J. 2008, 14, 6722-6773
12. B. M. Trost, G. Dong, Chem. Eur. J. 2009, 15, 6910-6919.
13. L. M. Stanley, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 8971-8983
14. L. M. Stanley, J. F. Hartwig, Angew. Chem. 2009, 121, 7981-7984
15. Angew. Chem. Int. Ed. 2009, 48, 7841-7844
16. W. Liu, D. Zhang, S. Zheng, Y. Yue, D. Liu, X. Zhao, Eur. J. Org. Chem. 2011, 6288-6293
17. M. Zhang, X. Guo, S. Zheng, X. Zhao, Tetrahedron Lett. 2012, 53, 6995-6998
18. W. Liu, X. Zhang, L. Dai, S. You, Angew. Chem. 2012, 124, 5273-5277
19. Angew. Chem. Int. Ed. 2012, 51, 5183-5187
20. B. M. Trost, M. Osipov, G. Dong, Org. Lett. 2012, 14, 2254-2257.
21. M. N. S. Rad, A. Khalafi-Nezhad, S. Behrouz, M. A. Faghihi, A. Zare, A. Parhami, Tetrahedron 2008, 64, 1778-1785
22. R. Ghosh, A. Sarkar, J. Org. Chem. 2011, 76, 8508-8512.
23. B. M. Trost, Chem. Rev. 1996, 96, 395-422
24. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921-2943
25. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264-303
26. Angew. Chem. Int. Ed. 2008, 47, 258-297.
27. L. E. Overman, J. Am. Chem. Soc. 1976, 98, 2901-2910
28. L. E. Overman, C. E. Owen, M. M. Pavan, Org. Lett. 2003, 5, 1809-1812
29. B. M. Trost, M. Osipov, G. Dong, J. Am. Chem. Soc. 2010, 132, 15800-15807
30. B. M. Trost, T. Zhang, J. D. Sieber, Chem. Sci. 2010, 1, 427-440.
31. A. Leitner, S. Shekhar, M. J. Pouy, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15506-15514
32. R. Weihofen, O. Tverskoy, G. Helmchen, Angew. Chem. 2006, 118, 5673-5676
33. Angew. Chem. Int. Ed. 2006, 45, 5546-5549
34. Y. Yamashita, A. Gopalarathnam, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7508-7509
35. K. Ye, H. He, W. Liu, G. Helmchen, S. You, J. Am. Chem. Soc. 2011, 133, 19006-19014
36. M. Lafrance, M. Roggen, E. M. Carreira, Angew. Chem. 2012, 124, 3527-3530
37. Angew. Chem. Int. Ed. 2012, 51, 3470-3473.
38. P. A. Evans, J. E. Robinson, J. Nelson, J. Am. Chem. Soc. 1999, 121, 6761-6762
39. P. A. Evans, J. E. Robinson, K. K. Moffett, Org. Lett. 2001, 3, 3269-3271
40. M. Lautens, K. Fagnou, D. Yang, J. Am. Chem. Soc. 2003, 125, 14884-14892
41. P. A. Evans, E. A. Clizbe, J. Am. Chem. Soc. 2009, 131, 8722-8723.
42. Y. Matsushima, K. Onitsuka, T. Kondok, T. Mitsudo, S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405-10406
43. M. D. Mbaye, B. Demerseman, J. Renaud, L. Toupet, C. Bruneau, Angew. Chem. 2003, 115, 5220-5222
44. Angew. Chem. Int. Ed. 2003, 42, 5066-5068
45. B. Plietker, Angew. Chem. 2006, 118, 6200-6203
46. Angew. Chem. Int. Ed. 2006, 45, 6053-6056.
47. G. Liu, S. S. Stahl, J. Am. Chem. Soc. 2007, 129, 6328-6335
48. G. Liu, G. Yin, L. Wu, Angew. Chem. 2008, 120, 4811-4814
49. Angew. Chem. Int. Ed. 2008, 47, 4733-4736
50. S. A. Reed, M. C. White, J. Am. Chem. Soc. 2008, 130, 3316-3318
51. R. I. McDonald, S. S. Stahl, Angew. Chem. 2010, 122, 5661-5664
52. Angew. Chem. Int. Ed. 2010, 49, 5529-5532
53. G. Yin, Y. Wu, G. Liu, J. Am. Chem. Soc. 2010, 132, 11978-11987
54. A. B. Weinstein, S. S. Stahl, Angew. Chem. 2012, 124, 11673-11677
55. Angew. Chem. Int. Ed. 2012, 51, 11505-11509
56. S. M. Paradine, M. C. White, J. Am. Chem. Soc. 2012, 134, 2036-2039.
57. B. M. Trost, Science 1991, 254, 1471-1477
58. T. Newhouse, P. S. Baran, R. W. Hoffmann, Chem. Soc. Rev. 2009, 38, 3010-3021.
59. R. Zimmer, C. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067-3125
60. J. Johnson, R. G. Bergman, J. Am. Chem. Soc. 2001, 123, 2923-2924
61. B. M. Trost, C. Jäkel, B. Plietker, J. Am. Chem. Soc. 2003, 125, 4438-4439
62. S. S. Kinderman, R. Gelder, J. H. Maarseveen, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, J. Am. Chem. Soc. 2004, 126, 4100-4101
63. N. Nishina, Y. Yamamoto, Angew. Chem. 2006, 118, 3392-3395
64. Angew. Chem. Int. Ed. 2006, 45, 3314-3317
65. R. L. Lalonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2352-2453
66. I. S. Kim, M. J. Krische, Org. Lett. 2008, 10, 513-515
67. T. Kawamoto, S. Hirabayashi, X. Guo, T. Nishimura, T. Hayashi, Chem. Commun. 2009, 3528-3530
68. S. B. Han, I. S. Kim, H. Han, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 6916-6917
69. J. Moran, A. Preetz, R. A. Mesch, M. J. Krische, Nat. Chem. 2011, 3, 287-290
70. K. L. Butler, M. Tragni, R. A. Widenhoefer, Angew. Chem. 2012, 124, 5265-5268
71. Angew. Chem. Int. Ed. 2012, 51, 5175-5178.
72. L. Besson, J. Goré, B. Gazes, Tetrahedron Lett. 1995, 36, 3857-3860
73. M. Al-Masum, M. Meguro, Y. Yamamoto, Tetrahedron Lett. 1997, 38, 6071-6074.
74. Y. Yamamoto, M. Al-Masum, N. Asao, J. Am. Chem. Soc. 1994, 116, 6019-6020
75. M. Al-Masum, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 3809-3810
76. L. M. Lutete, I. Kadota, Y. Yamamoto, J. Am. Chem. Soc. 2004, 126, 1622-1623.
77. A. Lumbroso, P. Koschker, N. R. Vautravers, B. Breit, J. Am. Chem. Soc. 2011, 133, 2386-2389
78. P. Koschker, A. Lumbroso, B. Breit, J. Am. Chem. Soc. 2011, 133, 20746-20749
79. A. Lumbroso, N. Abermil, B. Breit, Chem. Sci. 2012, 3, 789-793
80. M. L. Cooke, K. Xu, B. Breit, Angew. Chem. 2012, 124, 11034-11037
81. Angew. Chem. Int. Ed. 2012, 51, 10876-10879.
82. G. A. Ardizzoia, S. Brenna, G. LaMonica, A. Maspero, N. Masciocchi, M. Moret, Inorg. Chem. 2002, 41, 610-614
83. P. A. Evans, J. D. Nelson, J. Am. Chem. Soc. 1998, 120, 5581-5582
84. J. Wolf, H. Werner, Organometallics 1987, 6, 1164-1169
85. B. Wucher, M. Moser, S. A. Schumacher, F. Rominger, D. Kunz, Angew. Chem. 2009, 121, 4481-4485
86. Angew. Chem. Int. Ed. 2009, 48, 4417-4421.
87. G. Poli, G. Prestat, F. Liron, C. Kammerer-Pentier, Top. Organomet. Chem. 2012, 38, 1-64.