Pd-catalyzed regio- and stereoselective cyclization-heck reaction of monoesters of 1,2-allenyl phosphonic acids with alkenes

Organic Letters

Volumn 9, Issue 9, 2007, Pages 1703-1706

  Yu, Fei ^a   Lian, Xiongdong ^a   Ma, Shengming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34248345141     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0703478     Document Type: Article

References (73)

1. st Century; John Wiley & Sons: New York, 2004.
2. For reviews, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
3. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
4. (c) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
5. For some of the most recent publications, see: (a) Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751.
6. (b) Mariampillai, B.; Herse, C.; Lautens, M. Org. Lett. 2005, 7, 4745.
7. (c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
8. (d) Dubbaka, S. R.; Vogel, P. Chem.-Eur. J. 2005, 11, 2633.
9. (e) Arvela, B. K.; Leadbeater, N. E. J. Org. Chem. 2005, 70, 1786.
10. (f) Mata, Y.; Diéguez, M.; Pàmies, O.; Claver, C. Org. Lett. 2005, 7, 5597.
11. (g) Cui, X.; Li, Z.; Tao, C.; Xu, Y.; Li, J.; Liu, L.; Guo, Q. Org. Lett. 2006, 8, 2467.
12. (h) Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2003, 125, 3430.
13. (a) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
14. (b) Sohn, J.; Waizumi, N.; Zhong, M.; Rawal, V. J. Am. Chem. Soc. 2005, 127, 7290.
15. (c) Dounay, A. B.; Overman, L. E.; Wrobleski, A. D. J. Am. Chem. Soc. 2005, 127, 10186.
16. (d) Muraoka, N.; Mineno, M.; Itami, K.; Yoshida, J. J. Org. Chem. 2005, 70, 6933.
17. (e) Sengupta, S.; Drew, M. G. B.; Mukhopadhydy, R.; Achari, B.; Banerjee, A. Kr. J. Org. Chem. 2005, 70, 7694.
18. (f) Routier, S.; Merour, J.; Dias, N.; Lansiaux, A.; Bailly, C.; Lozach, O.; Meijer, L. J. Med. Chem. 2006, 49, 789.
19. For some of the most recent reviews on the chemistry of allenes, see: (a) Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004; Vols. 1 and 2.
20. (b) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
21. (c) Ma, S. Chem. Rev. 2005, 105, 2829.
22. (d) Ma, S. Acc. Chem. Res. 2003, 36, 701.
23. (e) Ma, S. Pure Appl. Chem. 2006, 78, 197.
24. For some of the most recent publications, see: (a) Jayanth, T. T.; Jeganmohan, M.; Cheng, M.; Chu, S.; Cheng, C. J. Am. Chem. Soc. 2006, 128, 2232.
25. (b) Wilson, J. E.; Fu, G. C. Angew. Chem., Int. Ed. 2006, 45, 1426.
26. (c) Ohno, H.; Kadoh, Y.; Fujii, N.; Tanaka, T. Org. Lett. 2006, 8, 947.
27. (d) Tonogaki, K.; Itami, K.; Yoshida, J. J. Am. Chem. Soc. 2006, 128, 1464.
28. (e) Morita, N.; Krause, N. Angew. Chem., Int. Ed. 2006, 45, 1897.
29. (f) Nishimura, T.; Hirabayashi, S.; Yasuhara, Y.; Hayashi, T. J. Am. Chem. Soc. 2006, 128, 2556.
30. (g) Närhi, K.; Franzén, J.; Bäckvall, J. E. J. Org. Chem. 2006, 71, 2914.
31. (h) Yu, C.; Youn, J.; Jung, J. Angew. Chem., Int. Ed. 2006, 45, 1553.
32. (i) Mae, M.; Hong, J. A.; Xu, B.; Hammond, G. B. Org. Lett. 2006, 8, 479.
33. (a) Meguro, M.; Kamijo, S.; Yamamoto, Y. Tetrahedron Lett. 1996, 37, 7453.
34. (b) Ohno, H.; Anzai, M.; Toda, A.; Ohishi, S.; Fujii, N.; Tanaka, T.; Takemoto, Y.; Ibuka, T. J. Org. Chem. 2001, 66, 4904.
35. (c) Walkup, R. D.; Guan, L.; Kim, Y. S.; Kim, S. W. Tetrahedron Lett. 1995, 36, 3805.
36. (d) Kang, S. K.; Kim, K. J. Org. Lett. 2001, 3, 511.
37. (e) Ma, S.; Shi, Z. J. Org. Chem. 1998, 63, 6387.
38. (f) Ma, S.; Zhao, S. J. Am. Chem. Soc. 2001, 123, 5578.
39. (g) Ma, S.; Gao, W. Synlett 2002, 65.
40. (a) Gamez, P.; Ariente, C.; Gore, J.; Cazes, B. Tetrahedron 1998, 54, 14835.
41. (b) Rutjes, F. P. J. T.; Tjen, K. C. M. F.; Wolf, L. B.; Karstens, W. F. J.; Schoemaker, H. E.; Hiemstra, H. Org. Lett. 1999, 1, 717.
42. (c) Ma, S.; Zhang, J. Chem. Commun. 2000, 117.
43. (d) Ma, S.; Zhao, S. Org. Lett. 2000, 2, 2495.
44. (e) Ma, S.; Jiao, N.; Yang, Q.; Zheng, Z. J. Org. Chem. 2004, 69, 6463.
45. (f) Ma, S.; Xie, H. J. Org. Chem. 2002, 67, 6575.
46. (g) Ma, S.; Gao, W. Org. Lett. 2002, 4, 2989.
47. (a) Kimura, M.; Tanaka, S.; Tamaru, Y. J. Org. Chem. 1995, 60, 3764.
48. (b) Ma, S.; Li, L. Org. Lett. 2000, 2, 941.
49. (c) Ma, S.; Yu, Z. J. Org. Chem. 2003, 68, 6149.
50. (d) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104.
51. (e) Ma, S.; Yu, F.; Gao, W. J. Org. Chem. 2003, 68, 5943.
52. Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955.
53. Ma, S.; Gu, Z.; Deng, Y. Chem. Commun. 2006, 94.
54. Ma, S.; Gu, Z. J. Am. Chem. Soc. 2005, 127, 6182.
55. Heck, R. F. Org. React. 1982, 27, 345.
56. (a) Darrow, J. W.; Drueckhammer, D. G. J. Org. Chem. 1994, 59, 2976.
57. (b) Monta, I.; Kunimoto, K.; Tsuda, M.; Tada, S. I.; Kise, M.; Kimura, K. Chem. Pharm. Bull. 1987, 35, 4144.
58. (c) Stewart, J. D.; Liotta, L. J.; Benkovic, S. J. Acc. Chem. Res. 1993, 26, 396.
59. (d) Collard, J.; Benezra, C. Tetrahedron Lett. 1982, 23, 3725.
60. (e) Racha, S.; Vargeese, C.; Vemishetti, P.; El-Subbagh, H. I.; Abushanab, E.; Panzica, R. P. J. Med. Chem. 1996, 39, 1130.
61. (a) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
62. (b) Christov, V. C.; Prodanov, B. Heterocycles 2002, 57, 1777.
63. (c) Macomber, R. S.; Krudy, G. A.; Seff, K.; Rendon-Diaz-Miron, L. E. J. Org. Chem. 1983, 48, 1425.
64. (d) Cristau, H. J.; Pirat, J. L.; Virieux, D.; Monbrum, J.; Ciptadi, C.; Bekro, Y. J. Organomet. Chem. 2005, 690, 2472.
65. (e) Stachel, H. D.; Hampl, B. Chem. Ber. 1981, 114, 405.
66. (f) Hah, J.; Lee, B.; Lee, S.; Lee, H. Tetrahedron Lett. 2003, 44, 5811.
67. (g) Abramovitch, R. A.; Konieczny, M.; Pennington, W.; Kanamatharaddy, S.; Vedachalam, M. J. Chem. Soc., Chem. Commun. 1990, 269.
68. (a) Ma, S.; Yu, F. Tetrahedron 2005, 61, 9896.
69. (b) Yasuhara, A.; Kaneko, M.; Sakamoto, T. Heterocycles 1998, 48, 1793.
70. (c) Goyal, M.; Nagahata, R.; Sugiyama, J.; Asai, M.; Ueda, M.; Takeuchi, K. J. Mol. Catal. Chem. A: Chem. 1999, 137, 147.
71. (d) Ma, S.; Wu, B.; Zhao, S. Org. Lett. 2003, 5, 4429.
72. (a) Ma, S.; Yu, Z. Org. Lett. 2003, 5, 1507.
73. (b) Ma, S.; Yu, Z.; Gu, Z. Eur. J. Chem. 2005, 11, 2351.