Regio- and stereoselective synthesis of multisubstituted vinylsilanes via zirconacycles

Organic Letters

Volumn 11, Issue 16, 2009, Pages 3546-3549

  Nishihara, Yasushi ^a   Saito, Daisuke ^a   Tanemura, Kenki ^a   Noyori, Shintaro ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 68949142762     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901236s     Document Type: Article

References (58)

1. (a) Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386-10387.
2. (b) Shimizu, M.; Nakamaki, C.; Shimono, K.; Schelper, M.; Kurahashi, T.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 12506-12507.
3. Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Tanemura, K.; Inoue, E.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634-12635.
4. For recent reports for utility of vinylsilanes in organic synthesis, see: (a) Gordillo, A.; de Jesus, E.; Lopez-Mardomingo, C. J. Am. Chem. Soc. 2009, 131, 4584-4585.
5. (b) Sugiyama, A.; Ohnishi, Y.; Nakaoka, M.; Nakao, Y.; Sato, H.; Sakaki, S.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 12975-12985.
6. (d) Zhang, H.; Song, Z.; Wang, C.; Bruneau, C.; Xi, Z. Tetrahedron Lett. 2008, 49, 624-627.
7. (e) Xi, Z.; Zhang, W.-X. Synlett 2008, 2557-2570.
8. (f) Li, D.; Liu, G.; Hu, Q.; Wang, C.; Xi, Z. Org. Lett. 2007, 9, 5433-5436.
9. (g) Park, J.-W.; Jun, C.-H. Org. Lett. 2007, 9, 4073-4076.
10. (a) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471-1478.
11. (b) Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; Chapter 10, pp421-454.
12. (c) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684-1688.
13. (d) Denmark, S. E.; Neuville, L.; Christy, M. E. L.; Tymonko, S. A. J. Org. Chem. 2006, 71, 8500-8509.
14. Sato, K.; Kira, M.; Sakurai, H. Tetrahedron Lett. 1989, 30, 4375-4378.
15. Li, L.; Navasero, N. Org. Lett. 2004, 6, 3091-3094.
16. (a) Hirabayashi, K.; Takahisa, E.; Nishihara, Y.; Mori, A.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 2409-2417.
17. (b) Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299-301.
18. (c) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342-5349.
19. (d) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835-846, and references cited therein.
20. Denmark, S. E.; Pan, W. T. Org. Lett. 2001, 3, 61-64.
21. Denmark, S. E.; Butler, C. R. Org. Lett. 2006, 8, 63-66.
22. For reviews, see: (a) Denmark, S. E.; Sweis, R. F. Chem. Pharm. Bull. 2002, 50, 1531-1541.
23. (b) Denmark, S. E.; Ober, M. E. Aldrichim. Acta 2003, 36 75-85.
24. Denmark, S.; Choi, J. J. Am. Chem. Soc. 1999, 121, 5821-5822.
25. Anderson, J. C.; Anguille, S.; Bailey, R. Chem. Commun. 2002, 2018-2019.
26. Trost, B. M.; Machacek, M. R.; Ball, Z. T. Org. Lett. 2003, 5, 1895-1898.
27. Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 138-139.
28. Itami, K.; Nokami, T.; Yoshida, J. Adv. Synth. Catal. 2002, 344, 441-451, and references cited therein.
29. (a) Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2004, 126, 13942-13944.
30. (b) Li, L.; Navasero, N. Org. Lett. 2006, 8, 3733-3736.
31. Nakao, Y.; Imanaka, H.; Sahoo, A. K.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 6952-6953.
32. Doyle, M. M.; Jackson, W. R.; Perlmutter, P. Aust. J. Chem. 1989, 42, 1907-1918.
33. Takahashi, T.; Nitto, Y.; Seki, T.; Saburi, M.; Negishi, E. Chem. Lett. 1990, 2259-2262.
34. For example, see: (a) Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623-626.
35. (b) Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058.
36. (c) Johnson, S. A.; Liu, F. Q.; Suh, M. C.; Zurcher, S.; Haufe, M.; Mao, S. S. H.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 4199-4211.
37. (d) Imabayashi, T.; Fujiwara, Y.; Nakao, Y.; Sato, H.; Sakaki, S. Organometallics 2005, 24, 2129-2140.
38. Miller, A. D.; McBee, J. L.; Tilley, T. D. J. Am. Chem. Soc. 2008, 130, 4992-4999.
39. Mori, A.; Takahisa, E.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Chem. Lett. 1998, 443-444.
40. Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005, 127, 8004-8005.
41. Potassium trimethylsilanolate has found use for activation of vinylsilanes: (a) Anderson, J. C.; Munday, R. H. J. Org. Chem. 2004, 69, 8971-8974.
42. (b) Denmark, S. E.; Sweis, R. F. J. Am. Chem. Soc. 2001, 123, 6439-6440.
43. Other Hiyama coupling for retention of configuration of (Z)-vinylsilanes: Tris(trimethylsilyl)vinylsilanes: Wnuk, S. F.; Garcia, P. I., Jr. Org. Lett. 2004, 6, 2047-2049.
44. Diethoxymethyvinylsilanes: Mori, A.; Takahisa.; Yamamura, Y.; Kato, T.; Mudalige, A. P.; Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T. Organometallics 2004, 23, 1755-1765.
45. Denmark, S.; Wehrli, D.; Choi, J. Org. Lett. 2000, 2, 2491-2494.
46. Denmark, S. E.; Sweis, R. F.; Wehrli, D. J. Am. Chem. Soc. 2004, 126, 4865-4875.
47. Takahashi, T.; Suzuki, N.; Kageyama, M.; Kondakov, D. Y.; Hara, R. Tetrahedron Lett. 1993, 34, 4811-4814.
48. (a) Erker, G.; Zwettler, R.; Kruger, C.; Hylakryspin, I.; Gleiter, R. Organometallics 1990, 9, 524-530.
49. (b) Hara, R.; Xi, Z.; Kotora, M.; Xi, C.; Takahashi, T. Chem. Lett. 1996, 1003-1004.
50. (a) Takahashi, T.; Hara, R.; Nishihara, Y.; Kotora, M. J. Am. Chem. Soc. 1996, 118, 5154-5155.
51. (b) Hara, R.; Nishihara, Y.; Landre, P. D.; Takahashi, T. Tetrahedron Lett. 1997, 38, 447-450.
52. Negishi, E.-i.; Van Horn, D. E. J. Am. Chem. Soc. 1977, 99, 3168-3170.
53. Hara, R.; Liu, Y.; Sun, W.-H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4103-4106.
54. (a) Takahashi, T.; Kotora, M.; Fischer, R.; Nishihara, Y.; Nakajima, K. J. Am. Chem. Soc. 1995, 117, 11039-11040.
55. (b) Takahashi, T.; Nishihara, Y.; Hara, R.; Huo, S.; Kotora, M. Chem. Commun. 1997, 1599-1600.
56. Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781-6786.
57. Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228-3229.
58. 2; see: Obora, Y.; Moriya, H.; Tokunaga, M.; Tsuji, Y. Chem. Commun. 2003, 2820-2821.