Enantioselective gold-catalyzed functionalization of unreactive sp 3 Ci-H bonds through a redox-neutral domino reaction

Chemistry - A European Journal

Volumn 17, Issue 11, 2011, Pages 3101-3104

  Zhou, Guanghua ^a   Liu, Feng ^a   Zhang, Junliang ^a,b  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

azepines; Ci H activation; enantioselectivity; furan; gold

Indexed keywords

AZEPINES; CI-H ACTIVATION; DOMINO REACTIONS; ENANTIOSELECTIVE; FUNCTIONALIZATIONS; FURAN; H-BONDS; HIGH ENANTIOSELECTIVITY; HIGH YIELD; TRIFLATES;

AROMATIC COMPOUNDS; CATALYSIS; ENANTIOSELECTIVITY; REACTION KINETICS;

GOLD;

EID: 79952133884     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100019     Document Type: Article

References (85)

1. For recent reviews on Ci-H activation, see
2. R. G. Bergman, Nature 2007, 446, 391-393
3. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238
4. K. Godula, D. Sames, Science 2006, 312, 67-72
5. J. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013-1025
6. H. M. L. Davies, Angew. Chem. 2006, 118, 6574-6577
7. Angew. Chem. Int. Ed. 2006, 45, 6422-6425.
8. 3 Ci-H bond activation, see
9. K. R. Campos, Chem. Soc. Rev. 2007, 36, 1069-1084
10. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654-2672.
11. B. DeBoef, S. J. Pastine, D. Sames, J. Am. Chem. Soc. 2004, 126, 6556-6557
12. S. J. Pastine, D. Sames, Org. Lett. 2005, 7, 5429-5431
13. S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180-12181
14. K. M. McQuaid, J. Z. Long, D. Sames, Org. Lett. 2009, 11, 2972-2975
15. K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2009, 131, 402-403
16. P. A. Vadola, D. Sames, J. Am. Chem. Soc. 2009, 131, 16525-16528
17. S. Yang, Z. Li, X. Jian, C. He, Angew. Chem. 2009, 121, 4059-4061
18. Angew. Chem. Int. Ed. 2009, 48, 3999-4001
19. K. Mori, T. Kawasaki, S. Sueoka, T. Akiyama, Org. Lett. 2010, 12, 1732-1735
20. D. Shikanai, H. Murase, T. Hata, H. Urabe, J. Am. Chem. Soc. 2009, 131, 3166-3167
21. I. D. Jurberg, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc. 2010, 132, 3543-3552
22. G. B. Bajracharya, N. K. Pahadi, I. D. Gridnev, Y. Yamamoto, J. Org. Chem. 2006, 71, 6204-6210
23. N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 10935-10941
24. S. J. Mahoney, D. T. Moon, J. Hollinger, E. Fillion, Tetrahedron Lett. 2009, 50, 4706-4709.
25. For the latest general reviews on gold-catalyzed reactions, see
26. A. S. K. Hashmi, Angew. Chem. 2008, 120, 6856-6858
27. Angew. Chem. Int. Ed. 2008, 47, 6754-6756
28. A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766-1775
29. N. Bongers, N. Krause, Angew. Chem. 2008, 120, 2208-2211
30. Angew. Chem. Int. Ed. 2008, 47, 2178-2181
31. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
32. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265
33. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442
34. N. Marion, S. P. Nolan, Chem. Soc. Rev. 2008, 37, 1776-1782
35. S. Wang, G. Zhang, L. Zhang, Synlett 2010, 692-706
36. R. Skouta, C.-J. Li, Tetrahedron 2008, 64, 4917-4938
37. S. M. Abu Sohel, R.-S. Liu, Chem. Soc. Rev. 2009, 38, 2269-2281.
38. For a review of enantioselective gold(I) catalysis, see
39. R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382-5391, and references therein. For other recent leading examples since 2008, see
40. R. L. LaLonde, Z. J. Wang, M. Mba, A. D. Lackner, F. D. Toste, Angew. Chem. 2010, 122, 608-611
41. Angew. Chem. Int. Ed. 2010, 49, 598-601
42. A. Z. González, F. D. Toste, Org. Lett. 2010, 12, 200-203
43. H. Teller, S. Flügge, R. Goddard, A. Fürstner, Angew. Chem. 2010, 122, 1993-1997
44. Angew. Chem. Int. Ed. 2010, 49, 1949-1953
45. C.-M. Chao, M. R. Vitale, P. Y. Toullec, J.-P. Genêt, V. Michelet, Chem. Eur. J. 2009, 15, 1319-1323
46. C.-M. Chao, D. Beltrami, P. Y. Toullec, V. Michelet, Chem. Commun. 2009, 6988-6990
47. Z. Zhang, S. D. Lee, R. A. Widenhoefer, J. Am. Chem. Soc. 2009, 131, 5372-5373
48. I. Alonso, B. Trillo, F. Lõpez, S. Montserrat, G. Ujaque, L. Castedo, A. Lledõs, J. L. Mascareñas, J. Am. Chem. Soc. 2009, 131, 13020-13030
49. M. Uemura, I. D. G. Watson, M. Katsukawa, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 3464-3465
50. I. D. G. Watson, S. Ritter, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 2056-2057
51. F. Kleinbeck, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 9178-9179
52. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9697-9701
53. Angew. Chem. Int. Ed. 2009, 48, 9533-9537.
54. For reviews on the tert-amino effect, see
55. O. Meth-Cohn, H. Suschitzky, Adv. Heterocycl. Chem. 1972, 14, 211-278
56. W. Verboom, D. N. Reinhoudt, Recl. Trav. Chim. Pays-Bas 1990, 109, 311-324
57. O. Meth-Cohn, Adv. Heterocycl. Chem. 1996, 65, 1-37
58. J. M. Quintela, Recent Res. Dev. Org. Chem. 2003, 7, 259-278
59. P. Matyus, O. Elias, P. Tapolcsanyi, A. Polonka-Balint, B. Halasz-Dajka, Synthesis 2006, 2625-2639. For selected recent examples, see
60. C. Zhang, C. Kanta De, R. Mal, D. Seidel, J. Am. Chem. Soc. 2008, 130, 416-417
61. J. Barluenga, M. Fanãnás-Mastral, F. Aznar, C. Valdés, Angew. Chem. 2008, 120, 6696-6699
62. Angew. Chem. Int. Ed. 2008, 47, 6594-6597
63. J. C. Ruble, A. R. Hurd, T. A. Johnson, D. A. Sherry, M. R. Barbachyn, P. L. Toogood, G. L. Bundy, D. R. Graber, G. M. Kamilar, J. Am. Chem. Soc. 2009, 131, 3991-3992.
64. S. Murarka, C. Zhang, M. D. Konieczynska, D. Seidel, Org. Lett. 2009, 11, 129-132
65. S. Murarka, I. Deb, C. Zhang, D. Seidel, J. Am. Chem. Soc. 2009, 131, 13226-13227.
66. Y. K. Kang, S. M. Kim, D. Y. Kim, J. Am. Chem. Soc. 2010, 132, 11847-11849.
67. For selected reviews and highlights dealing with the synthesis of furans, see
68. R. C. D. Brown, Angew. Chem. 2005, 117, 872-874
69. Angew. Chem. Int. Ed. 2005, 44, 850-852
70. D. M. D'Souza, T. J. J. Müller, Chem. Soc. Rev. 2007, 36, 1095-1108
71. X. L. Hou, Z. Yang, K-S. Yu, H. N. C. Wong, in Progress in Heterocyclic Chemistry, Vol.19 (Eds.:, G.W. Gribble, J.A. Joule,), Pergamon, Oxford, 2008, p. 176.
72. For recent reviews and selected examples of azepine synthesis, see
73. J. B. Bremner, in Progress in Heterocyclic Chemistry, Vol.17, Pergamon, Oxford, 2005, p. 389
74. Chemistry of Heterocyclic Compounds: Azepines, Part2, Vol.43 (Ed.:, A. Rosowsky,), Wiley-Interscience, New York, 2008; selected recent examples see
75. H. He, W.-B. Liu, L.-X. Dai, S.-L. You, Angew. Chem. 2010, 122, 1538-1541
76. Angew. Chem. Int. Ed. 2010, 49, 1496-1499
77. L. Cui, L. Ye, L. Zhang, Chem. Commun. 2010, 46, 3351-3353
78. S. Sakami, M. Maeda, K. Kawai, T. Aoki, K. Kawamura, H. Fujii, K. Hasebe, M. Nakajima, T. Endo, S. Ueno, T. Ito, J. Kamei, H. Nagase, J. Med. Chem. 2008, 51, 4404-4411
79. C. M. Yea, C. E. Allan, D. M. Ashworth, J. Barnett, J. Med. Chem. 2008, 51, 8124-8134
80. N. D. Shapiro, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 9244-9245
81. W. H. Pearson, W.-K. Fang, J. Org. Chem. 2000, 65, 7158-7174.
82. G. Zhou, J. Zhang, Chem. Commun. 2010, 46, 6593-6595.
83. F. Liu, D. Qian, L. Li, X. Zhao, J. Zhang, Angew. Chem. 2010, 122, 6819-6822
84. Angew. Chem. Int. Ed. 2010, 49, 6669-6672.
85. CCDC-796888 (2 b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.