Synthesis of 1Z,4E,6E-Triene Derivatives by Chemo- and Regioselective Iridium-Catalyzed Dienylation of ortho-Aminostyrenes with Dienyl Carbonates

Asian Journal of Organic Chemistry

Volumn 2, Issue 3, 2013, Pages 244-249

  Ye, Ke Yin ^a   Dai, Li Xin ^a   You, Shu Li ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Allylic alkylation; Dienylation; Iridium; Regioselectivity; Trienes

Indexed keywords

EID: 84897661212     PISSN: 21935807     EISSN: 21935807     Source Type: Journal    
DOI: 10.1002/ajoc.201300015     Document Type: Article

References (69)

1. B. M. Trost, D. L. VanVranken, Chem. Rev. 1996, 96, 395;
2. B. M. Trost, M. L. Crawley, Chem. Rev. 2003, 103, 2921;
3. Z. Lu, S. Ma, Int. Ed. 2008, 47, 258;
4. S. Förster, G. Helmchen, U. Kazmaier in Catalytic Asymmetric Synthesis, 3rded. (Ed.: I. Ojima), Wiley, New Jersey, 2010, p.497.
5. B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1994, 116, 4089;
6. Y. Matsushima, K. Onitsuka, T. Kondo, T.-a. Mitsudo, S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405;
7. C. A. Kiener, C. Shu, C. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 14272;
8. K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. Int. Ed. 2004, 43, 2426;
9. K. Tissot-Croset, D. Polet, A. Alexakis, Angew. Chem. 2004, 116, 2480;
10. J. W. Faller, J. C. Wilt, Org. Lett. 2005, 7, 633;
11. S. Spiess, C. Welter, G. Franck, J.-P. Taquet, G. Helmchen, Chem. Int. Ed. 2008, 47, 7652;
12. L. M. Stanley, J. F. Hartwig, J. Am. Chem. Soc. 2009, 131, 8971;
13. T. Kanayama, K. Yoshida, H. Miyabe, Y. Takemoto, Angew. Chem. Int. Ed. 2003, 42, 2054;
14. T. Kanayama, K. Yoshida, H. Miyabe, Y. Takemoto, Angew. Chem. 2003, 115, 2100;
15. H. Miyabe, A. Matsumura, K. Moriyama, Y. Takemoto, Org. Lett. 2004, 6, 4631.
16. B. M. Trost, J. Quancard, J. Am. Chem. Soc. 2006, 128, 6314;
17. C. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew. Chem. Int. Ed. 2007, 46, 3139;
18. C. Defieber, M. A. Ariger, P. Moriel, E. M. Carreira, Angew. Chem. 2007, 119, 3200;
19. Y. Yamashita, A. Gopalarathnam, J. F. Hartwig, J. Am. Chem. Soc. 2007, 129, 7508;
20. S. Tanaka, T. Seki, M. Kitamura, Angew. Chem. Int. Ed. 2009, 48, 8948;
21. M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed. 2009, 48, 9533;
22. M. Roggen, E. M. Carreira, J. Am. Chem. Soc. 2010, 132, 11917;
23. H. Yamamoto, E. Ho, K. Namba, H. Imagawa, M. Nishizawa, Chem. Eur. J. 2010, 16, 11271;
24. K. Miyata, H. Kutsuna, S. Kawakami, M. Kitamura, Angew. Chem. Int. Ed. 2011, 50, 4649;
25. M. Lafrance, M. Roggen, E. M. Carreira, Angew. Chem. Int. Ed. 2012, 51, 3470;
26. M. Schafroth, D. Sarlah, S. Krautwald, E. M. Carreira, J. Am. Chem. Soc. 2012, 134, 20276.
27. B. M. Trost, E. Keinan, J. Am. Chem. Soc. 1978, 100, 7779;
28. B. M. Trost, E. Keinan, J. Org. Chem. 1979, 44, 3451;
29. P. G. Andersson, J.-E. Bäckvall, J. Org. Chem. 1991, 56, 5349;
30. Y. I. M. Nilsson, P. G. Andersson, J.-E. Bäckvall, J. Am. Chem. Soc. 1993, 115, 6609; For Pd-catalyzed branched-selective alkylation with dienyl substrates, see:
31. W.-H. Zheng, N. Sun, X.-L. Hou, Org. Lett. 2005, 7, 5151.
32. B. M. Trost, M.-H. Hung, J. Am. Chem. Soc. 1984, 106, 6837;
33. B. M. Trost, R. C. Bunt, J. Am. Chem. Soc. 1998, 120, 70;
34. S. Basak, U. Kazmaier, Org. Lett. 2008, 10, 501;
35. S. Basak, U. Kazmaier, Eur. J. Org. Chem. 2008, 4169.
36. B. M. Trost, G. B. Tometzki, M.-H. Hung, J. Am. Chem. Soc. 1987, 109, 2176.
37. B. M. Trost, S. Hildbrand, K. Dogra, J. Am. Chem. Soc. 1999, 121, 10416.
38. R. Takeuchi, K. Tanabe, Angew. Chem. Int. Ed. 2000, 39, 1975;
39. G. Lipowsky, N. Miller, G. Helmchen, Angew. Chem. Int. Ed. 2004, 43, 4595;
40. G. Lipowsky, G. Helmchen, Chem. Commun. 2004, 116;
41. C. Shu, A. Leitner, J. F. Hartwig, Angew. Chem. Int. Ed. 2004, 43, 4797;
42. A. Leitner, C. Shu, J. F. Hartwig, Org. Lett. 2005, 7, 1093;
43. S. Shekhar, B. Trantow, A. Leitner, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 11770.
44. H. Miyabe, Y. Takemoto, Synlett 2005, 1641;
45. R. Takeuchi, S. Kezuka, Synthesis 2006, 3349;
46. G. Helmchen, A. Dahnz, P. Dübon, M. Schelwies, R. Weihofen, Chem. Commun. 2007, 675;
47. G. Helmchen in Iridium Complexes in Organic Synthesis; (Eds.: L.A. Oro, C. Claver), Wiley-VCH, Weinheim, Germany, 2009, p.211;
48. J. F. Hartwig, L. M. Stanley, Acc. Chem. Res. 2010, 43, 1461;
49. J. F. Hartwig, M. J. Pouy, Top. Organomet. Chem. 2011, 34, 169;
50. W.-B. Liu, J.-B. Xia, S.-L. You, Top. Organomet. Chem. 2012, 38, 155;
51. P. Tosatti, A. Nelson, S. P. Marsden, Org. Biomol. Chem. 2012, 10, 3147.
52. L. M. Stanley, C. Bai, M. Ueda, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 8918;
53. M. Gärtner, S. Mader, K. Seehafer, G. Helmchen, J. Am. Chem. Soc. 2011, 133, 2072;
54. J. F. Teichert, M. Fañanás-Mastral, B. L. Feringa, Angew. Chem. Int. Ed. 2011, 50, 688;
55. N. Gao, S. Zheng, W. Yang, X. Zhao, Org. Lett. 2011, 13, 1514;
56. P. Tosatti, A. J. Campbell, D. House, A. Nelson, S. P. Marsden, J. Org. Chem. 2011, 76, 5495;
57. W. Chen, J. F. Hartwig, J. Am. Chem. Soc. 2012, 134, 15249.
58. C.-X. Zhuo, W.-B. Liu, Q.-F. Wu, S.-L. You, Chem. Sci. 2012, 3, 205;
59. Q.-F. Wu, C. Zheng, S.-L. You, Angew. Chem. Int. Ed. 2012, 51, 1680;
60. Q.-F. Wu, C. Zheng, S.-L. You, Angew. Chem. 2012, 124, 1712;
61. W.-B. Liu, C. Zheng, C.-X. Zhuo, L.-X. Dai, S.-L. You, J. Am. Chem. Soc. 2012, 134, 4812.
62. H. He, W.-B. Liu, L.-X. Dai, S.-L. You, J. Am. Chem. Soc. 2009, 131, 8346;
63. H. He, W.-B. Liu, L.-X. Dai, S.-L. You, Angew. Chem. 2010, 122, 1538; Angew. Chem. Int. Ed. 2010, 49, 1496;
64. H. He, W.-B. Liu, L.-X. Dai, S.-L. You, Angew. Chem. 2010, 122, 1538;
65. K.-Y. Ye, H. He, W.-B. Liu, L.-X. Dai, G. Helmchen, S.-L. You, J. Am. Chem. Soc. 2011, 133, 19006; Recently, Carreira and co-workers reported an Ir-catalyzed asymmetric allylic vinylation reaction with vinyl trifluoroborates:
66. J. Y. Hamilton, D. Sarlah, E. M. Carreira, J. Am. Chem. Soc. 2013, 135, 994.
67. A. Leitner, S. Shekhar, M. J. Pouy, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 15506.
68. CCDC885171 contains the supplementary crystallographic data for (1Z, 4E, 6E)-3ab. These data can be obtained free of charge from the Cambridge Crystallographic Data Center via www.cam.ac.uk/data_request/cif.
69. A. Rimkus, N. Sewald, Synthesis 2004, 135.