A zirconium promenade - An efficient tool in organic synthesis

Synlett

Volumn , Issue 4, 2006, Pages 501-514

  Marek, Ilan ^a   Chinkov, Nicka ^a,b   Levin, Anat ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^b ETH ZURICH   (Switzerland)

Author keywords

Allylic C H activation; Allylzirconocene; Dienyl zirconocene; Elimination; Isomerization

Indexed keywords

ALCOHOL DERIVATIVE; OLEIC ACID; UNSATURATED FATTY ACID; VINYL DERIVATIVE; ZIRCONIUM DERIVATIVE; ZIRCONOCENE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ELIMINATION REACTION; ISOMERIZATION; METALLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33645008213     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-932483     Document Type: Article

References (69)

1. (a) Hart, D. W.; Schwartz, J. J. Am. Chem. Soc. 1974, 96, 8115.
2. (b) Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679.
3. (c) Blackburn, T. F.; Labinger, J. A.; Schwartz, J. Tetrahedron Lett. 1975, 3041.
4. (d) Labinger, J. A.; Hart, D. W.; Seibert, W. E. III; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 3851.
5. (e) Bertelo, C. A.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 228.
6. (f) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1977, 99, 638.
7. (g) Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1979, 101, 3521.
8. For recent reviews, see: (h) Lipshutz, B. H.; Pfeiffer, S. S.; Noson, K.; Tomioka, T. Hydrozirconation and further Transmetalation Reactions, In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002, 110.
9. Wipf, P. Hydrozirconation and its Applications, In Metallocenes in Regio- and Stereoselective Synthesis, In Topics in Organometallic Chemistry, Vol. 8; Takahashi, T., Ed.; Springer: Berlin, 2004, 1.
10. Kautzner, B.; Wailes, P. C.; Weigold, H. J. Chem. Soc., Chem. Commun. 1969, 1105.
11. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
12. Zakharkin, L. I.; Okhlobystin, O. Y. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1958, 1236.
13. Brown, H. C.; Zweifel, G. J. Am. Chem. Soc. 1967, 89, 561.
14. For recent very nice examples of boron migration, see: (a) Lhermitte, F.; Knochel, P. Angew. Chem. Int. Ed. 1998, 37, 2460.
15. (b) Bromm, L. O.; Laaziri, H.; Lhermitte, F.; Harms, K.; Knochel, P. J. Am. Chem. Soc. 2000, 122, 10218.
16. (c) Hupe, E.; Denisenko, D.; Knochel, P. Tetrahedron 2003, 59, 9187.
17. Cooper, G. D.; Finkbeiner, H. L. J. Org. Chem. 1962, 27, 1493.
18. Asinger, F.; Fell, B.; Hanssen, R. Chem. Ber. 1964, 97, 2515.
19. Annby, U.; Karlsson, S.; Gronowitz, S.; Hallberg, A.; Alvhall, J.; Svenson, R. Acta Chem. Scand. 1993, 47, 425.
20. Alvhall, J.; Gronowitz, S.; Hallberg, A. Chem. Scr. 1988, 28, 285.
21. Alvhall, J.; Gronowitz, S.; Hallberg, A. Chem. Scr. 1985, 25, 393.
22. Karlsson, S.; Hallberg, A.; Gronowitz, S. Chem. Scr. 1988, 28, 185.
23. Karlsson, S.; Hallberg, A.; Gronowitz, S. J. Am. Oil Chem. Soc. 1989, 66, 1815.
24. (a) Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755.
25. (b) Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124.
26. (c) Negishi, E.; Huo, S. Synthesis and Reactivity of Zirconocene Derivatives, In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002, 1.
27. Maye, J. P.; Negishi, E. Tetrahedron Lett. 1993, 34, 3359.
28. Negishi, E.; Maye, J. P.; Choueiry, D. Tetrahedron 1995, 51, 4447.
29. Chinkov, N.; Levin, A.; Marek, I. Angew. Chem. Int. Ed. 2006, 45, 465.
30. (a) Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299.
31. (b) Fujita, K.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2004, 126, 6776; and references cited therein.
32. (c) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031.
33. (d) Marek, I. Carbometallation Reactions, In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 395.
34. (e) Szymoniak, J.; Moise, C. Synthesis and Reactivity of Allyltitanium Derivatives, In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002, 451.
35. Bertus, P.; Gandon, V.; Szymoniak, J. Chem. Commun. 2000, 171.
36. (a) Yamamoto, Y.; Maruyama, K. Tetrahedron Lett. 1981, 22, 2895.
37. (b) Mishima, K.; Yasuda, H.; Asami, T.; Nakamura, A. Chem. Lett. 1983, 219.
38. (a) Rousset, C. J.; Swanson, D. R.; Lamaty, F.; Negishi, E. Tetrahedron Lett. 1989, 30, 5105.
39. (b) Ito, H.; Nakamura, T.; Taguchi, T.; Hanzawa, Y. Tetrahedron 1992, 51, 4507.
40. Gandon, V.; Laroche, C.; Szymoniak, J. Tetrahedron Lett. 2003, 44, 4827.
41. (a) Liard, A.; Marek, I. J. Org. Chem. 2000, 65, 7518.
42. (b) Liard, A.; Chechik, H.; Farhat, S.; Morlender-Vais, N.; Averbuj, C.; Marek, I. J. Organomet. Chem. 2001, 624, 26.
43. (c) Ganchegui, B.; Bertus, P.; Szymoniak, J. Synlett 2001, 123.
44. Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
45. Chinkov, N.; Chechik, H.; Majumdar, S.; Liard, A.; Marek, I. Synthesis 2002, 2473.
46. Negishi, E.; Choueiry, D.; Nguyen, T. B.; Swanson, D. R.; Suzuki, N.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 9751.
47. Takahashi, T.; Fujimoto, T.; Seki, T.; Saburi, M.; Uchida, Y.; Rousset, C. J.; Negishi, E. J. Chem. Soc., Chem. Commun. 1990, 182.
48. (a) Mintz, E. A.; Ward, A. S.; Tice, D. S. Organometallics 1985, 4, 1308.
49. (b) Ward, A. S.; Mintz, E. A.; Kramer, M. P. Organometallics 1988, 7, 8.
50. (a) Takahashi, T.; Suzuki, N.; Kageyama, M.; Nitto, Y.; Saburi, M.; Negishi, E. Chem. Lett. 1991, 1579.
51. (b) Takahashi, T.; Nitto, Y.; Seki, T.; Saburi, M.; Negishi, E. Chem. Lett. 1990, 2259.
52. Farhat, S.; Marek, I. Angew. Chem. Int. Ed. 2002, 41, 1410.
53. Farhat, S.; Zouev, I.; Marek, I. Tetrahedron 2004, 60, 1329.
54. (a) Owen, D. R.; Whitby, R. J. Synthesis 2005, 2061.
55. (b) Barluenga, J.; Sanz, R.; Fanañas, F. J. Z. Naturforsch., B: Chem. Sci. 1995, 50, 312.
56. (c) Takahashi, T.; Kondakov, D. Y.; Xi, Z.; Suzuki, N. J. Am. Chem. Soc. 1995, 117, 5871.
57. (d) Takahashi, T.; Xi, Z.; Fischer, R.; Huo, S.; Xi, C.; Nakajima, K. J. Am. Chem. Soc. 1997, 119, 4561.
58. (a) Barluenga, J.; Rodriguez, F.; Alvarez-Rodrigo, L.; Fanañas, F. J. Chem. Soc. Rev. 2005, 34, 762.
59. (b) Barluenga, J.; Rodriguez, F.; Alvarez-Rodrigo, L.; Zapico, J. M.; Fanañas, F. J. Chem. Eur. J. 2004, 10, 109.
60. (c) Barluenga, J.; Alvarez-Rodrigo, L.; Rodriguez, F.; Fanañas, F. J. Angew. Chem. Int. Ed. 2004, 43, 3932.
61. (d) Barluenga, J.; Rodriguez, F.; Alvarez-Rodrigo, L.; Fanañas, F. J. Chem. Eur. J. 2004, 10, 101.
62. Alexakis, A.; Normant, J. F. Isr. J. Chem. 1984, 24, 113.
63. Chinkov, N.; Majumdar, S.; Marek, I. J. Am. Chem. Soc. 2002, 124, 10282.
64. Chinkov, N.; Majumdar, S.; Marek, I. J. Am. Chem. Soc. 2003, 125, 13258.
65. Rosenthal, U.; Burlakov, V. V. Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002, 355.
66. Nitschke, J. R.; Zurcher, S.; Tilley, D. T. J. Am. Chem. Soc. 2000, 122, 10345.
67. Takahashi, T.; Swanson, D. R.; Negishi, E. Chem. Lett. 1987, 623.
68. Fryzuk, M. D.; Bates, G. S.; Stone, C. Tetrahedron Lett. 1986, 27, 1537.
69. Rozema, M. J.; Knochel, P. Tetrahedron Lett. 1991, 32, 1855.