Synthesis and stereochemistry of planar-chiral cyclopentadienyl complexes of late transition metals

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 60, Issue 8, 2002, Pages 752-761

  Onitsuka, Kiyotaka ^a   Matsushima, Yuji ^a   Takahashi, Shigetoshi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Allytic substitution; Asymmetric catalysis; Asymmetric induction; Cyclopentadienyl complex; Late transition metal; Metal centered chirality; Optical resolution; Planar chirality

Indexed keywords

ALKYLATION; AMINATION; CATALYSIS; COMPLEXATION; DERIVATIVES; PHOSPHORUS COMPOUNDS; RECRYSTALLIZATION (METALLURGY); REMOVAL; RUTHENIUM COMPOUNDS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ANCHOR PHOSPHINE LIGANDS; CHIRAL CYCLOPENTADIENYL; CYCLOPENTADIENES; DIASTEREOSELECTIVITY; ENANTIOMER; LATE TRANSITION METALS; METHYL ESTER;

ORGANOMETALLICS;

EID: 0036702431     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.60.752     Document Type: Article

References (83)

1. (a) R. Noyori, "Asymmetric Catalysis in Organic Synthesis" Wiley, New York, 1994
2. (b) J. Seyden-Penne, "Chiral Auxiliaries and Ligands in Asymmetric Synthesis", Wiley, New York, 1995
3. (a) A. Togni, T. Hayash (eds), "Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science", Wiley-VCH: Weinheim, 1995
4. (b) A. Togni, R. L. Halterman (eds), "Metallocenes: Synthesis · Reactivity · Applications", Wiley-VCH, Weinheim, 1998, Vol. 1-2
5. R. L. Halterman, Chem. Rev., 92, 965 (1992)
6. M. Hatanaka, Y. Himeda, I. Ueda, J. Chem. Soc., Perkin Trans. 1, 1993, 2269
7. M. Uno, K. Ando, N. Komatsuzaki, S. Takahashi, J. Chem. Soc., Chem. Commun., 1992, 964
8. T. Katayama, Y. Morimoto, M. Yuge, M. Uno, S. Takahashi, Organometallics, 18, 3087 (1999)
9. (a) N. Komatsuzaki, M. Uno, H. Kikuchi, S. Takahashi, Chem. Lett., 1996, 677
10. (b) Y. Matsushima, N. Komatsuzaki, Y. Ajioka, M. Yamamoto, H. Kikuchi, Y. Takata, N. Dodo, K. Onitsuka, M. Uno, S. Takahashi Bull. Chem. Soc. Jpn., 74, 527 (2001)
11. Y. Ajioka, Y. Matsushima, K. Onitsuka, H. Yamazaki, S. Takahashi, J. Organomet. Chem., 617-618, 601 (2001)
12. Y. Morimoto, K. Ando, M. Uno, S. Takahashi, Chem. Lett., 1996, 887
13. (a) M. Uno, K. Ando, N. Komatsuzaki, T. Tanaka, S. Sawada, S. Takahashi, J. Chem. Soc., Chem. Commun., 1993, 1549
14. (b) M. Uno, K. Ando, N. Komatsuzaki, T. Tsuda, T. Tanaka, M. Sawada, S. Takahashi, J. Organomet. Chem., 473, 303 (1994)
15. (c) M. Uno, K. Shirai, K. Ando, N. Komatsuzaki, T. Tanaka, M. Sawada, S. Takahashi, Chem. Lett., 1995, 7
16. N. Komatsuzaki, M. Uno, K. Shirai, T. Tanaka, M. Sawada, S. Takahashi, J. Organomet. Chem., 498, 53 (1995)
17. (a) M. Uno, N. Komatsuzaki, K. Shirai, S. Takahashi, J. Organomet. Chem., 462, 343 (1993)
18. (b) N. Komatsuzaki, M. Uno, K. Shirai, Y. Takai, T. Tanaka, M. Sawada, S. Takahashi, Bull. Chem. Soc. Jpn., 69, 17 (1996)
19. H. Buntenschön, Chem. Rev., 100, 1527 (2000)
20. N. Dodo, Y. Matsushima, M. Uno, K. Onitsuka, S. Takahashi, J. Chem. Soc., Dalton Trans., 2000, 35
21. K. Kamikawa, M. Furusyo, T. Uno, Y. Sato, A. Konoo, G. Bringmann, M. Uemura, Org. Lett., 3, 3667 (2001)
22. N. Komatsuzaki, H. Kikuchi, M. Yamamoto, M. Uno, S. Takahashi, Chem. Lett., 1998, 445
23. Y. Matsushima, K. Onitsuka, S. Takahashi, Chem. Lett., 2000, 760
24. (a) M. Crocker, M. Green, C. E. Morton, K. R. Nagle, A. G. Orpen, J. Chem. Soc., Dalton Trans., 1985, 2145
25. (b) C. Gemel, K. Mereiter, R. Schmid, K. Kirchner, Organometallics, 15, 532 (1996)
26. (a) H. Brunner, Adv. Organomet. Chem., 18, 151 (1980)
27. (b) G. Consiglio, F. Morandini, Chem. Rev., 87, 761 (1987)
28. (c) H. Brunner, Angew. Chem., Int. Ed., 38, 1194 (1999)
29. (a) S. G. Davis, Aldlichim. Acta, 23, 31 (1990)
30. (b) M. Brookhart, Y. Liu, E. W. Goldmman, D. A. Tmmers, and G. D. Williams, J. Am. Chem. Soc., 113, 927 (1991)
31. (c) J. W. Faller, M. R. Mazzieri, J. T. Nguyen, J. Parr, M. Tokunaga, Pure Appl. Chem., 66, 1463 (1991)
32. (d) J. A. Gladysz, B. J. Boone, Angew. Chem., Int. Ed. Engl., 36, 550 (1997)
33. (a) D. L. Davis, J. Fawcett, S. A. Garratt, D. R. Russell, Chem. Commun., 1997, 1531
34. (b) D. Carmona, F. J. Lahoz, S. Elipe, L. A. Oro, M. P. Lamata, F. Viguri, C. Mir, C. Cativiela, M. P. López-Ram de Víu, Organometallics, 17, 2986 (1998)
35. (c) J. W. Faller, B. J. Grimmond, D. G. D'Alliessi, J. Am. Chem. Soc., 123, 2525 (2001)
36. (a) T. A. Mobley, R. G. Bergman, J. Am. Chem. Soc., 120, 3253 (1998)
37. (b) Y. Kataoka, A. Shibahara, Y. Saito, T. Yamagata, K. Tani, Organometallics, 17, 4338 (1998)
38. (c) Y. Kataoka, Y. Iwato, T. Yamagata, K. Tani, ibid., 18, 5423 (1999)
39. (d) Y. Kataoka, Y. Iwato, A. Shibahara, T. Yamagata, K. Tani, Chem. Commun., 2000, 841
40. Y. Morinoto, K. Ando, M. Uno, S. Takahashi, Chem. Commun., 1997, 1795
41. T. G. Attig, A. Wojcicki, J. Organomet. Chem., 82, 397 (1974)
42. T. Katayama, Y. Matsushima, K. Onitsuka, S. Takahashi, Chem. Commun., 200, 2337
43. K. Onitsuka, N. Dodo, Y. Matsushima, S. Takahashi, Chem. Commun., 2001, 521
44. (a) Y. Kataoka, Y. Saito, K. Nagata, K. Kitamura, A. Shibahara, K. Tani, Chem. Lett., 1995, 833
45. (b) U. Koelle, K. Bücken, U. Englert, Organometallics, 15, 1376 (1996)
46. (c) D. Carmona, F. J. Lahoz, L. A. Oro, M. P. Lamata, F. Viguri, E. San José, ibid., 15, 3096 (1996)
47. (d) Y. Nishibayashi, I. Takei, M. Hidai, ibid., 16, 3091 (1997)
48. (e) A. A. H. van der Zeijden, J. Jimenez, C. Mattheis, C. Wagner, K. Merzweiler, Eur. J. Inorg. Chem., 1999, 1919
49. (f) A. J. Davenport, D. L. Davis, J. Fawcett, S. A. Garratt, D. R. Russell, Chem. Commun., 1999, 2331
50. (g) B. M. Trost, B. Vidal, M. Thommen, Chem. Eur. J., 5, 1055 (1999)
51. (h) D. Carmona, F. J. Lahoz, R. Atencio, L. A. Oro, M. P. Lamata, F. Viguri, E. San José, C. Vega, J. Reyes, F. Joó, Á. Kathó, ibid., 5, 1544 (1999)
52. (i) S. Fernandez, M. Pfeffer, V. Ritleng, C. Sirlin, Organometallics, 18, 2390 (1999)
53. (j) J. W. Faller, B. P. Patel, M. A. Albrizzio, M. Curtis, ibid., 18, 3096 (1999)
54. (k) C. Slugovc, W. Simanko, K. Mereiter, R. Schmid, K. Kirchner, L. Xiao, W. Weissensteiner, ibid., 18, 3865 (1999)
55. (l) V. Ritleng, J. P. Sutter, M. Pfeffer, C. Sirlin, Chem. Commun., 2000, 129
56. (m) H. Brunner, T. Zwack, Organometallics, 19, 2423 (2000)
57. K. Onitsuka, Y. Ajioka, Y. Matsushima, S. Takahashi, Organometallics, 20, 3274 (2001)
58. (a) S. K. Mandal, A. R. Chakravarty, J. Chem. Soc., Dalton Trans., 1992, 1627
59. (b) idem, Inorg. Chem., 32, 3851 (1993)
60. (c) H. Brunner, R. Oeschey, B. Nuber, Angew. Chem., Int. Ed. Engl., 33, 866 (1994)
61. (d) idem, Inorg. Chem., 34, 3349 (1995)
62. (e) idem, J. Chem. Soc., Dalton Trans., 1996, 1499
63. (a) T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev., 98, 2599 (1998)
64. (b) 59, 170 (2001)
65. B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev., 101, 2067 (2001)
66. (a) S.-W. Zhang, T. Mitsudo, T. Kondo, Y. Watanabe, J. Organomet. Chem., 450, 197 (1993)
67. (b) T. Kondo, H. Ono, N. Satake, T. Mitsudo, Y. Watanabe, Organometallics, 14, 1945 (1995)
68. (c) Y. Morisaki, T. Kondo, T. Mitsudo, ibid., 18, 4742 (1999)
69. (d) T. Kondo, Y. Morisaki, S. Uenoyama, K. Wada, T. Mitsudo, J. Am. Chem. Soc., 121, 8657 (1999)
70. (a) T. Hayashi, "Catalytic Asymmetric Synthesis", ed. by I. Ojima, VCH, New York, 1993, p 325
71. (b) O. Reiser, Angew. Chem., Int. Ed. Engl., 32, 547 (1993)
72. (c) B. M. Trost, D. L. Van Vranken, Chem. Rev., 96, 395 (1996)
73. (d) M. Johannsen, K. A. Jørgensen, ibid., 98, 1689 (1998)
74. (e) S. J. Sesay, J. M. J. Williams, Adv. Asymmetric Synth., 3, 235 (1998)
75. (f) G. Helmchen, J. Organomet. Chem., 576, 203 (1999)
76. (a) G. C. Lloyd-Jones, A. Pfaltz, Angew. Chem., Int. Ed. Engl., 32, 547 (1993)
77. (b) B. M. Trost, I. Hachiya, J. Am. Chem. Soc., 120, 1104 (1998)
78. (c) F. Glorius, A. Pfaltz, Org. Lett., 1, 141 (1999)
79. (d) B. Bartels, G. Helmchen, Chem. Commun., 1999, 741
80. (e) A. J. Blacker, M. L. Clark, J. M. J. Williams, M. S. Loft, ibid., 1999, 913
81. (f) P. A. Evans, L. J. Kennedy, J. Am. Chem. Soc., 123, 1234 (2001)
82. Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo, S. Takahashi, J. Am. Chem. Soc., 123, 10405 (2001)
83. K. Hiraki, T. Matsunaga, H. Kawano, Organometallics, 13, 1878 (1994)