Synthetic methods for multiply substituted butadiene-containing building blocks

Synlett

Volumn , Issue 17, 2008, Pages 2557-2570

  Xi, Zhenfeng ^a   Zhang, Wen Xiong ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

Conjugation; Electrophiles; Functionalized dienes; Halobutadienes; Lithiobutadienes

Indexed keywords

1 HALOBUTA 1,3 DIENE DERIVATIVE; 1 LITHIOBUTA 1,3 DIENE DERIVATIVE; 1,3 BUTADIENE; 1,4 DIHALOBUTA 1,3 DIENE DERIVATIVE; 1,4 DILITHIOBUTA 1,3 DIENE DERIVATIVE; BUTA 1,3 DIENYL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; SYNTHESIS;

EID: 55449119441     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078257     Document Type: Article

References (99)

1. Langer, P.; Freiberg, W. Chem. Rev. 2004, 104, 4125.
2. (a) Li, D.; Liu, G.; Hu, Q.; Wang, C.; Xi, Z. Org. Lett. 2007, 9, 5433.
3. (b) Morita, R.; Shirakawa, E.; Tsuchimoto, T.; Kawakami, Y. Org. Biomol. Chem. 2005, 3, 1263.
4. (c) Ramachandran, P. V.; Rudd, M. T.; Reddy, M. V. R. Tetrahedron Lett. 2005, 46, 2547.
5. (d) Zeng, X.; Qian, M.; Hu, Q.; Negishi, E. Angew. Chem. Int. Ed. 2004, 43, 2259.
6. (e) Walsh, J. G.; Furlong, P. J.; Gilheany, D. G. J. Chem. Soc., Perkin Trans. 1 1999, 3657.
7. (f) Kasatkin, A.; Whitby, R. J. J. Am. Chem. Soc. 1999, 121, 7039.
8. (g) Martin, M.-E.; Planchenault, D.; Huet, F. Tetrahedron 1995, 51, 4985.
9. (h) Mo, X.-S.; Huang, Y.-Z. Tetrahedron Lett. 1995, 36, 3539.
10. (i) Walsh, J. G.; Furlong, P. J.; Gilheany, D. G. J. Chem. Soc., Chem. Commun. 1994, 67.
11. (j) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
12. (k) Stork, G.; Chan, T. Y.; Breault, G. A. J. Am. Chem. Soc. 1992, 114, 7578.
13. (l) Sieburth, S. M.; Fensterbank, L. J. Org. Chem. 1992, 57, 5279.
14. (m) Reich, H. J.; Shah, S. K.; Chow, F. J. Am. Chem. Soc. 1979, 101, 6648.
15. Crombie, L.; Fisher, D. Tetrahedron Lett. 1985, 26, 2481.
16. Alami, M.; Gueugnot, S.; Domingues, E.; Linstrumelle, G. Tetrahedron 1995, 51, 1209.
17. For recent accounts on the reaction chemistry of 1-lithio-1,3-dienes and 1,4-dilithio-1,3-dienes, see: (a) Xi, Z. Bull. Chem. Soc. Jpn. 2007, 80, 1021.
18. (b) Xi, Z. Eur. J. Org. Chem. 2004, 2773.
19. See also: (c) Foubelo, F.; Yus, M. Curr. Org. Chem. 2005, 9, 459.
20. (d) Varela, J. A.; Saá, C. Chem. Rev. 2003, 103, 3787.
21. (a) Wang, C.; Luo, Q.; Sun, H.; Guo, X.; Xi, Z. J. Am. Chem. Soc. 2007, 129, 3094.
22. (b) Wang, C.; Yuan, J.; Li, G.; Wang, Z.; Zhang, S.; Xi, Z. J. Am. Chem. Soc. 2006, 128, 4564.
23. (c) Liu, L.; Wang, Z.; Zhao, F.; Xi, Z. J. Org. Chem. 2007, 72, 3484.
24. (d) Fang, H.; Li, G.; Mao, G.; Xi, Z. Chem. Eur. J. 2004, 10, 3444.
25. (e) Wang, C.; Song, Q.; Xi, Z. Tetrahedron 2004, 60, 5207.
26. (f) Li, G.; Fang, H.; Zhang, S.; Xi, Z. Tetrahedron Lett. 2004, 45, 8399.
27. (g) Li, G.; Fang, H.; Xi, Z. Tetrahedron Lett. 2003, 44, 8705.
28. (h) Chen, J.; Song, Q.; Xi, Z. Tetrahedron Lett. 2002, 43, 3533.
29. (i) Song, Q.; Li, Z.; Chen, J.; Wang, C.; Xi, Z. Org. Lett. 2002, 4, 4627.
30. (j) Chen, J.; Song, Q.; Li, P.; Guan, H.; Jin, X.; Xi, Z. Org. Lett. 2002, 4, 2269.
31. (k) Chen, J.; Song, Q.; Wang, C.; Xi, Z. J. Am. Chem. Soc. 2002, 124, 6238.
32. (l) Xi, Z.; Song, Q.; Chen, J.; Guan, H.; Li, P. Angew. Chem. Int. Ed. 2001, 40, 1913.
33. (m) Song, Q.; Chen, J.; Jin, X.; Xi, Z. J. Am. Chem. Soc. 2001, 123, 10419.
34. (n) Xi, Z.; Song, Q. J. Org. Chem. 2000, 65, 9157.
35. For preparative methods of 1-halo-1,3-diene derivatives, see: (a) Liu, G.; Song, Z.; Wang, C.; Xi, Z. Chin. J. Org. Chem. 2007, 27, 837.
36. (b) Takahashi, T.; Sun, W.-H.; Xi, C.; Ubayama, H.; Xi, Z. Tetrahedron 1998, 54, 715.
37. (c) Ubayama, H.; Sun, W.-H.; Xi, Z.; Takahashi, T. Chem. Commun. 1998, 1931.
38. (d) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871.
39. Takahashi, T.; Xi, Z.; Fisher, R.; Huo, S.; Xi, C.; Nakajima, K. J. Am. Chem. Soc. 1997, 119, 4561.
40. (a) Ahmar, M.; Duyck, C.; Fleming, I. Pure Appl. Chem. 1994, 66, 2049.
41. (b) Hudrlik, P. F.; Kassim, A. M.; Agwaramgbo, E. L. O.; Doonquah, K. A.; Roberts, R. R.; Hudrlik, A. M. Organometallics 1993, 12, 2367.
42. (c) Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57.
43. (d) Asaoka, M.; Shima, K.; Takei, H. J. Chem. Soc., Chem. Commun. 1988, 430.
44. (a) Xi, Z.; Song, Z.; Liu, G.; Liu, X.; Takahashi, T. J. Org. Chem. 2006, 71, 3154.
45. (b) Xi, Z.; Liu, X.; Lu, J.; Bao, F.; Fan, H.; Li, Z.; Takahashi, T. J. Org. Chem. 2004, 69, 8547.
46. (a) Wang, Z.; Lu, X.; Lei, A.; Zhang, Z. J. Org. Chem. 1998, 63, 3806.
47. (b) Zhao, L.; Lu, X. Org. Lett. 2002, 4, 3903.
48. (c) Lu, X. Top. Catal. 2005, 35, 73.
49. See also: (d) Xiao, W.; Vasapollo, G.; Alper, H. J. Org. Chem. 1999, 64, 2080.
50. (e) Wei, X.; Taylor, R. J. K. J. Org. Chem. 2000, 65, 616.
51. (f) Deagostino, A.; Prandi, C.; Zavattaro, C.; Venturello, P. Eur. J. Org. Chem. 2006, 2463.
52. (g) Chen, S.; Wang, J. J. Org. Chem. 2007, 72, 4993.
53. (a) Huang, J.; Zou, L.; Jiang, H. Angew. Chem. Int. Ed. 2006, 45, 1945.
54. (b) Liu, H.; Jiang, H.; Xu, L.; Zhan, H. Tetrahedron Lett. 2007, 48, 8371.
55. (a) Shi, Y.; Peterson, S. M.; Haberaecker, W. W. III.; Slum, S. A. J. Am. Chem. Soc. 2008, 130, 2168.
56. See also: (b) Wang, C. Y.; Xi, Z. Chem. Soc. Rev. 2007, 36, 1395.
57. For preparative methods of 1,4-dihalo-1,3-diene derivatives, see: (a) Xi, C.; Huo, S.; Afifi, T. H.; Hara, R.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4099.
58. (b) Hill, J. E.; Balaich, G.; Fanwick, P. E.; Rothwell, I. P. Organometallics 1993, 12, 2911.
59. (c) Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
60. (d) Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870.
61. (e) Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
62. Ubayama, H.; Xi, Z.; Takahashi, T. Chem. Lett. 1998, 517.
63. Yamaguchi, S.; Jin, R.-Z.; Tamao, K.; Sato, F. J. Org. Chem. 1998, 63, 10060.
64. (a) Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1984, 106, 6422.
65. (b) Nugent, W. A.; Thorn, D. L.; Harlow, R. L. J. Am. Chem. Soc. 1987, 109, 2788.
66. Komeev, S. M.; Kaufmann, D. E. Synthesis 2002, 491.
67. Block, E.; Guo, C.; Thiruvazhi, M.; Toscano, P. J. J. Am. Chem. Soc. 1994, 116, 9403.
68. (a) Li, J. H.; Liang, Y.; Xie, Y. J. Org. Chem. 2004, 69, 8125.
69. See also: (b) Cai, M.; Zhou, Z.; Wang, P. Synthesis 2006, 789.
70. (c) Ye, X.; Wang, P.; Cai, M. J. Chem. Res., Synop. 2007, 319.
71. (a) Ananikov, V. P.; Mitchenko, S. A.; Beletskaya, I. P. Russ. J. Org. Chem. (Engl. Transi.) 2002, 38, 636.
72. (b) Ananikov, V. P.; Mitchenko, S. A.; Beletskaya, I. P. J. Organomet. Chem. 2001, 636, 175.
73. Fleming, F. F.; Wang, Q. Chem. Rev. 2003, 103, 2035.
74. Takayanagi, H.; Kitano, Y.; Morinaka, Y. J. Org. Chem. 1994, 59, 2700.
75. (a) Bennani, Y. L. J. Org. Chem. 1996, 61, 3542.
76. (b) Kleijn, H.; Westmijze, H.; Meijer, J.; Vermeer, P. J. Organomet. Chem. 1981, 206, 257.
77. (c) Westmijze, H.; Kleijn, H.; Vermeer, P. Synthesis 1978, 454.
78. (a) Swartz, C. R.; Parkin, S. R.; Bullock, J. E.; Anthony, J. E.; Mayer, A. C.; Malliaras, G. G. Org. Lett. 2005, 7, 3163.
79. (b) Kawai, H.; Katoono, R.; Fujiwara, K.; Tsuji, T.; Suzuki, T. Chem. Eur. J. 2005, 11, 815.
80. (c) Prochazka, M.; Siroky, M. Collect. Czech. Chem. Commun. 1983, 48, 1765.
81. Wang, C.; Wang, C.; Wang, Q.; Wang, Z.; Sun, H.; Guo, X.; Xi, Z. Chem. Eur. J. 2007, 13, 6484.
82. Amundsen, L. H.; Nelson, L. S. J. Am. Chem. Soc. 1951, 73, 242.
83. For a review on the electrophilic cyclization of unsaturated amides, see: Robin, S.; Rousseau, G. Tetrahedron 1998, 54, 13681.
84. Blot, V.; Reboul, V.; Metzner, P. J. Org. Chem. 2004, 69, 1196.
85. (a) Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432.
86. (b) Cherry, K.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Abarbri, M. Tetrahedron Lett. 2004, 45, 2063.
87. Wang, C.; Lu, J.; Mao, G.; Xi, Z. J. Org. Chem. 2005, 70, 5150.
88. (a) Wang, Z.; Fang, H.; Xi, Z. Tetrahedron 2006, 62, 6967.
89. (b) Fang, H.; Song, Q.; Wang, Z.; Xi, Z. Tetrahedron Lett. 2004, 45, 5159.
90. (a) Xi, Z.; Zhang, W.-X.; Song, Z.; Zheng, W.; Kong, F.; Takahashi, T. J. Org. Chem. 2005, 70, 8785.
91. (b) Xi, Z.; Zhang, W.-X.; Takahashi, T. Tetrahedron Lett. 2004, 45, 2427.
92. Johnson, A. W.; Kaska, W. C.; Starzewski, K. A. O.; Dixon, D. A. In Ylides and Imines of Phosphorus; Wiley-Interscience: New York, 1993, 314.
93. Wang, C.; Wang, Z.; Liu, L.; Wang, C.; Liu, G.; Xi, Z. J. Org. Chem. 2006, 71, 8565.
94. Wakefield, B. J. In Organolithium Methods; Academic: London, 1988, 82-88.
95. Deniau, E.; Enders, D. Tetrahedron Lett. 2002, 43, 8055.
96. (a) Wang, C.; Mao, G.; Wang, Z.; Xi, Z. Eur. J. Org. Chem. 2007, 1267.
97. (b) Mao, G.; Wang, C.; Chen, J.; Muramatsu, A.; Xi, Z. Tetrahedron Lett. 2005, 46, 5369.
98. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
99. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.