Cu-Promoted [2 + 2] cycloaddition of 1,4-bisallenes

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1366-1369

  Kitagaki, Shinji ^a   Kajita, Mikihito ^a   Narita, Syu ^a   Mukai, Chisato ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYNE; ALLENE; AMINE; BICYCLO COMPOUND; COPPER; INORGANIC SALT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ALKADIENES; ALKYNES; AMINES; BICYCLO COMPOUNDS; CATALYSIS; COPPER; CYCLIZATION; MOLECULAR STRUCTURE; SALTS;

EID: 84858690706     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300096u     Document Type: Article

References (66)

1. Murakami, M.; Matsuda, T. Cycloadditions of Allenes. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, pp 727-816.
2. Ma, S. Chem. Rev. 2005, 105, 2829-2872
3. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Soc. Rev. 2010, 39, 783-816
4. Aubert, C.; Fensterbank, L.; Garcia, P.; Malacria, M.; Simonneau, A. Chem. Rev. 2011, 111, 1954-1993
5. Ohno, H.; Mizutani, T.; Kadoh, Y.; Aso, A.; Miyamura, K.; Fujii, N.; Tanaka, T. J. Org. Chem. 2007, 72, 4378-4389
6. Alcaide, B.; Almendros, P.; Aragoncillo, C.; Redondo, M. C.; Torres, M. R. Chem. - Eur. J. 2006, 12, 1539-1546
7. Hansen, T. V.; Skattebøl, L.; Stenstrøm, Y. Tetrahedron 2003, 59, 3461-3466
8. Padwa, A.; Lipka, H.; Watterson, S. H.; Murphree, S. S. J. Org. Chem. 2003, 68, 6238-6250
9. Lutteke, G.; Kleinnijenhuis, R. A.; Jacobs, I.; Wrigstedt, P. J.; Correia, A. C. A.; Nieuwenhuizen, R.; Hue, B. T. B.; Goubitz, K.; Peschar, R.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2011, 3146-3155
10. Miao, R.; Gramani, S. G.; Lear, M. J. Tetrahedron Lett. 2009, 50, 1731-1733
11. Winkler, J. D.; Ragains, J. R. Org. Lett. 2006, 8, 4031-4033
12. Gulías, M.; Collado, A.; Trillo, B.; López, F.; Oñate, E.; Esteruelas, M. A.; Mascareñas, J. L. J. Am. Chem. Soc. 2011, 133, 7660-7663
13. Alcarazo, M.; Stork, T.; Anoop, A.; Thiel, W.; Fürstner, A. Angew. Chem., Int. Ed. 2010, 49, 2542-2546
14. Zhao, J.-F.; Loh, T.-P. Angew. Chem., Int. Ed. 2009, 48, 7232-7235
15. Luzung, M. R.; Mauleón, P.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 12402-12403
16. Brummond, K. M.; Osbourn, J. M. Beilstein J. Org. Chem. 2011, 7, 601-605
17. Siebert, M. R.; Osbourn, J. M.; Brummond, K. M.; Tantillo, D. J. J. Am. Chem. Soc. 2010, 132, 11952-11966
18. Ovaska, T. V.; Kyne, R. E. Tetrahedron Lett. 2008, 49, 376-378
19. Mukai, C.; Hara, Y.; Miyashita, Y.; Inagaki, F. J. Org. Chem. 2007, 72, 4454-4461
20. Jiang, X.; Ma, S. Tetrahedron 2007, 63, 7589-7595
21. Oh, C. H.; Gupta, A. K.; Park, D. I.; Kim, N. Chem. Commun. 2005, 5670-5672
22. Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. - Eur. J. 2009, 15, 9987-9989
23. Saito, N.; Tanaka, Y.; Sato, Y. Org. Lett. 2009, 11, 4124-4126
24. Oh, C. H.; Kim, A. Synlett 2008, 777-781
25. Matsuda, T.; Kadowaki, S.; Goya, T.; Murakami, M. Synlett 2006, 575-578
26. Oh, C. H.; Park, D. I.; Jung, S. H.; Reddy, V. R.; Gupta, A. K.; Kim, Y. M. Synlett 2005, 2092-2094
27. Ohno, H.; Mizutani, T.; Kadoh, Y.; Miyamura, K.; Tanaka, T. Angew. Chem., Int. Ed. 2005, 44, 5113-5115
28. Cao, H.; Van Ornum, S. G.; Deschamps, J.; Flippen-Anderson, J.; Laib, F.; Cook, J. M. J. Am. Chem. Soc. 2005, 127, 933-943
29. Shen, Q.; Hammond, G. B. J. Am. Chem. Soc. 2002, 124, 6534-6535
30. Garratt, P. J.; Neoh, S. B. J. Am. Chem. Soc. 1975, 97, 3255-3257
31. Bui, B. H.; Schreiner, P. R. Eur. J. Org. Chem. 2006, 4187-4192
32. Jiang, X.; Cheng, X.; Ma, S. Angew. Chem., Int. Ed. 2006, 45, 8009-8013
33. Lu, P.; Ma, S. Chin. J. Chem. 2010, 28, 1600-1606
34. Hong, Y.-T.; Yoon, S.-K.; Kang, S.-K.; Yu, C.-M. Eur. J. Org. Chem. 2004, 4628-4635
35. Kim, S. M.; Park, J. H.; Kang, Y. K.; Chung, Y. K. Angew. Chem., Int. Ed. 2009, 48, 4532-4535
36. For 1,6-bisallenes, see: Shimizu, T.; Sakamaki, K.; Kamigata, N. Tetrahedron Lett. 1997, 38, 8529-8532
37. Inagaki, F.; Narita, S.; Hasegawa, T.; Kitagaki, S.; Mukai, C. Angew. Chem., Int. Ed. 2009, 48, 2007-2011
38. Kawamura, T.; Inagaki, F.; Narita, S.; Takahashi, Y.; Hirata, S.; Kitagaki, S.; Mukai, C. Chem. - Eur. J. 2010, 16, 5173-5183
39. Inagaki, F.; Kitagaki, S.; Mukai, C. Synlett 2011, 594-614
40. Skattebøl, L.; Solomon, S. J. Am. Chem. Soc. 1965, 87, 4506-4513
41. Roth, W. R.; Erker, G. Angew. Chem., Int. Ed. Engl. 1973, 12, 503-504
42. Grimme, W.; Rother, H.-J. Angew. Chem., Int. Ed. Engl. 1973, 12, 505-506
43. Becher, G.; Skattebøl, L. Tetrahedron Lett. 1979, 20, 1261-1264
44. Roth, W. R.; Scholz, B. P.; Breuckmann, R.; Jelich, K.; Lennartz, H.-W. Chem. Ber. 1982, 115, 1934-1946
45. Toda, F.; Tanaka, K.; Sano, I.; Isozaki, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 1757-1758
46. Inanaga, J.; Sugimoto, Y.; Hanamoto, T. Tetrahedron Lett. 1992, 33, 7035-7038
47. Ezcurra, J. E.; Moore, H. W. Tetrahedron Lett. 1993, 34, 6177-6180
48. Braverman, S.; Duar, Y. J. Am. Chem. Soc. 1990, 112, 5830-5837
49. Höhn, J.; Weyerstahl, P. Chem. Ber. 1983, 116, 808-814
50. Staab, H. A.; Draeger, B. Chem. Ber. 1972, 105, 2320-2333
51. Kitagaki, S.; Okumura, Y.; Mukai, C. Tetrahedron 2006, 62, 10311-10320
52. Kitagaki, S.; Okumura, Y.; Mukai, C. Tetrahedron Lett. 2006, 47, 1849-1852
53. Kitagaki, S.; Katoh, K.; Ohdachi, K.; Takahashi, Y.; Shibata, D.; Mukai, C. J. Org. Chem. 2006, 71, 6908-6914
54. Aubert, P.; Princet, B.; Pornet, J. Synth. Commun. 1997, 27, 2615-2625
55. For the metal-catalyzed [2 + 2] cycloaddition, see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92
56. Jung, M. E.; Piizzi, G. Chem. Rev. 2005, 105, 1735-1766
57. Saito, S.; Hirayama, K.; Kabuto, C.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 10776-10780
58. Bouwkamp, M. W.; Bowman, A. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2006, 128, 13340-13341
59. Montaignac, B.; Vitale, M. R.; Ratovelomanana-Vidal, V.; Michelet, V. Eur. J. Org. Chem. 2011, 3723-3727
60. Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496-1502
61. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015
62. Crabbé, P.; Fillion, H.; André, D.; Luche, J.-L. J. Chem. Soc., Chem. Commun. 1979, 859-860
63. Searles, S.; Li, Y.; Nassim, B.; Lopes, M.-T. R.; Tran, P. T.; Crabbé, P. J. Chem. Soc., Perkin Trans. 1 1984, 747-751
64. Becker, K. B. Synthesis 1980, 238-240
65. Heimbach, P.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 206-208
66. Hojo, M.; Murakami, C.; Nakamura, S.; Hosomi, A. Chem. Lett. 1998, 331-332