Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes

Advanced Synthesis and Catalysis

Volumn 357, Issue 16-17, 2015, Pages 3611-3616

  Arif, Tanzeel ^a   Borie, Cyril ^a   Tintaru, Aura ^a   Naubron, Jean Valère ^b   Vanthuyne, Nicolas ^c   Bertrand, Michèle P ^a   Nechab, Malek ^a  

^a AIX MARSEILLE UNIV   (France)

^b Fédération de Chimie Marseille   (France)

^c AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

carbocycles; chirality; cuprates; cyclization; enynes

Indexed keywords

EID: 84954393117     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201500556     Document Type: Article

References (67)

1. D. Campolo, S. Gastaldi, C. Roussel, M. P. Bertrand, M. Nechab, Chem. Soc. Rev. 2013, 42, 8434-8466.
2. Modern Allene Chemistry, (Eds.:, N. Krause, A. S. K. Hashmi,), Wiley-VCH, Weinheim, 2004;
3. S. M. Ma, Chem. Rev. 2005, 105, 2829-2872.
4. E. Soriano, I. Fernandez, Chem. Soc. Rev. 2014, 43, 3041-3105.
5. For a review, see:, N. Krause, C. Winter, Chem. Rev. 2011, 111, 1994-2009.
6. P. Smirnov, J. Mathew, A. Nijs, E. Katan, M. Karni, C. Bolm, Y. Apeloig, I. Marek, Angew. Chem. 2013, 125, 13962-13966;
7. Angew. Chem. Int. Ed. 2013, 52, 13717-13721;
8. Y.-M. Wang, C. N. Kuzniewski, V. Rauniyar, C. Hoong, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 12972-12975;
9. B. Gockel, N. Krause, Org. Lett. 2006, 8, 4485-4488;
10. Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073;
11. G. R. Cook, W. Xu, Heterocycles 2006, 67, 215-232;
12. H. Ohno, K. Ando, H. Hamaguchi, Y. Takeoka, T. Tanaka, J. Am. Chem. Soc. 2002, 124, 15255-15266.
13. M. Nechab, D. Campolo, J. Maury, P. Perfetti, N. Vanthuyne, D. Siri, M. P. Bertrand, J. Am. Chem. Soc. 2010, 132, 14742-14744;
14. M. Nechab, E. Besson, D. Campolo, P. Perfetti, N. Vanthuyne, E. Bloch, R. Denoyel, M. P. Bertrand, Chem. Commun. 2011, 47, 5286-5288;
15. D. Campolo, A. Gaudel-Siri, D. Mondal, D. Siri, E. Besson, N. Vanthuyne, M. Nechab, M. P. Bertrand, J. Org. Chem. 2012, 77, 2773-2783;
16. S. Mondal, M. Nechab, D. Campolo, N. Vanthuyne, M. P. Bertrand, Adv. Synth. Catal. 2012, 354, 1987-2000;
17. S. Mondal, M. Nechab, N. Vanthuyne, M. P. Bertrand, Chem. Commun. 2012, 48, 2549-2551.
18. T. Arif, C. Borie, D. Mouysset, N. Vanthuyne, J.-V. Naubron, M. P. Bertrand, M. Nechab, Angew. Chem. 2014, 126, 3291-3295;
19. Angew. Chem. Int. Ed. 2014, 53, 3227-3231.
20. During the course of this work, an analogous strategy for the synthesis of achiral benzofulvenes was reported:, D.-Y. Li, Y. Wei, M. Shi, Chem. Eur. J. 2013, 19, 15682-15688.
21. Y. Qin, J. Lv, S. Luo, J.-P. Cheng, Org. Lett. 2014, 16, 5032-5035;
22. X. Zeng, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2011, 133, 17638-17640;
23. S. Mondal, R. K. Mohame, M. Manoharan, H. Phan, I. V. Alabugin, Org. Lett. 2013, 15, 5650-5653;
24. A. S. K. Hashmi, I. Braun, P. Nosel, J. Schadlich, M. Wieteck, M. Rudolph, F. Rominger, Angew. Chem. 2012, 124, 4532-4536;
25. Angew. Chem. Int. Ed. 2012, 51, 4456-4460;
26. X. Jia, D. A. Petrone, M. Lautens, Angew. Chem. 2012, 124, 10008-10010;
27. Angew. Chem. Int. Ed. 2012, 51, 9870-9872;
28. S. Guo, Y. Liu, Org. Biomol. Chem. 2008, 6, 2064-2070;
29. P. Dubé, F. D. Toste, J. Am. Chem. Soc. 2006, 128, 12062-12063.
30. G. Majetich, J. M. Shimkus, J. Nat. Prod. 2010, 73, 284-298;
31. D.-C. Oh, P. G. Williams, C. A. Kauffman, P. R. Jensen, W. Fenical, Org. Lett. 2006, 8, 1021-1024;
32. J. L. Wood, B. G. Pujanauski, R. Sharpong, Org. Lett. 2009, 11, 3128-3131.
33. E. Alcalde, N. Mesquida, J. Frigola, S. Lopez-Perez, R. Mercé, Org. Biomol. Chem. 2008, 6, 3795-3810;
34. E. Alcalde, N. Mesquida, S. Lopéz-Pérez, J. Frigola, R. Mercé, J. Med. Chem. 2009, 52, 675-687.
35. R. Leino, P. Lehmus, A. Lehtonen, Eur. J. Inorg. Chem. 2004, 3201-3222;
36. B. Q. Wang, Coord. Chem. Rev. 2006, 250, 242-258; for selected examples, see:
37. V. V. Izmer, A. Y. Lebedev, M. V. Nikulin, A. N. Ryabov, A. F. Asachenko, A. V. Lygin, D. A. Sorokin, A. Z. Voskoboynikov, Organometallics 2006, 25, 1217-1229;
38. M. Enders, R. Baker, Curr. Org. Chem. 2006, 10, 937-953.
39. M. Egi, K. Shimizu, M. Kamiya, Y. Ota, S. Akai, Chem. Commun. 2015, 51, 380-383.
40. A. Martinez, P. Garcia-Garcia, M. A. Fernandez-Rodriguez, F. Rodriguez, R. Sanz, Angew. Chem. 2010, 122, 4737-4741;
41. Angew. Chem. Int. Ed. 2010, 49, 4633-4637;
42. Z. Chai, T. J. Rainey, J. Am. Chem. Soc. 2012, 134, 3615-3618;
43. D. N. Tran, N. Cramer, Angew. Chem. 2011, 123, 11294-11298;
44. Angew. Chem. Int. Ed. 2011, 50, 11098-11102;
45. J. A. Brekan, T. E. Reynolds, K. A. Scheidt, J. Am. Chem. Soc. 2010, 132, 1472-1473;
46. F. Zhou, M. Yang, X. Lu, Org. Lett. 2009, 11, 1405-1408;
47. R. Shintani, K. Okamoto, T. Hayashi, Chem. Lett. 2005, 34, 1294-1295.
48. Modern Organocopper Chemistry, (Ed.:, N. Krause,), Wiley-VCH, Weinheim, 2002;
49. N. Yoshikai, E. Nakamura, Chem. Rev. 2012, 112, 2339-2372.
50. E. Piers, E. J. McEachern, P. A. Burns, Tetrahedron 2000, 56, 2753-2765;
51. V. Komanduri, F. Pedraza, M. J. Krische, Adv. Synth. Catal. 2008, 350, 1569-1576;
52. K. Tanino, K. Arakawa, M. Satoh, Y. Iwata, M. Miyashita, Tetrahedron Lett. 2006, 47, 861-864;
53. G. Balme, D. Bouyssi, N. Coia, Eur. J. Org. Chem. 2007, 19, 3158-3165;
54. P. A. Wender, A. W. White, J. Am. Chem. Soc. 1988, 110, 2218-2223.
55. T. den Hartog, A. Rudolph, B. Maciá, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2010, 132, 14349-14351;
56. Y. Suzuki, R. Yazaki, N. Kumagai, M. Shibasaki, Chem. Eur. J. 2011, 17, 11998-12001;
57. P. Liu, Y. Fukui, P. Tian, Z.-T. He, C.-Y. Sun, N.-Y. Wu, G.-Q. Lin, J. Am. Chem. Soc. 2013, 135, 11700-11703;
58. K. Li, A. Alexakis, Chem. Eur. J. 2007, 13, 3765-3771.
59. K. Nilson, C. Ullenius, Tetrahedron 1994, 50, 13173-13180;
60. Y. Yamamoto, S. Nishii, T. Ibuka, J. Chem. Soc. Chem. Commun. 1987, 1572-1573;
61. K. Yamamoto, H. Ogura, J.-I. Jukuta, H. Inoue, K. Hamada, Y. Sugiyama, S. Yamada, J. Org. Chem. 1998, 63, 4449-4458.
62. Y. Shi, J. Huang, Y.-F. Yang, L.-Y. Wu, Y.-N. Niu, P. F. Huo, X.-Y. Liu, Y. M. Liang, Adv. Synth. Catal. 2009, 351, 141-146.
63. N2 reaction of the vinylcuprate on the leaving group was described by Okuda, see:, Y. Okuda, Y. Morizawa, K. Oshima, H. Nozaki, Tetrahedron Lett. 1984, 25, 2483-2486.
64. N. Krause, R. Wagner, A. Gerold, J. Am. Chem. Soc. 1994, 116, 381-382.
65. S. Mondal, J.-V. Naubron, D. Campolo, M. Giorgi, M. P. Bertrand, M. Nechab, Chirality 2013, 25, 832-839.
66. For a recent review see:, B. Heasley, Curr. Org. Chem. 2014, 18, 641-686.
67. Diastereomeric ratios of 3:1 to 4:1 were reached in a recent report on the hydrogenation of aminoindenes:, B. Gourdet, M. E. Rudkin, H. W. Lam, Org. Lett. 2010, 12, 2554-2557.