A new roate to cationic half-sandwich ruthenium(II) complexes with chiral cyclopentadienylphosphane ligands

European Journal of Inorganic Chemistry

Volumn , Issue 11, 2004, Pages 2244-2252

  Doppiu, Angelino ^a   Salzer, Albrecht ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric catalysis; Constrained geometry ligands; Cyclopentadienyl ligands; P ligands; Ruthenium

Indexed keywords

ACETONITRILE; ENANTIOSELECTIVITY; KETONES; LITHIUM COMPOUNDS; PHOSPHORUS COMPOUNDS; RUTHENIUM COMPOUNDS;

ASYMMETRIC CATALYSIS; CATIONICS; CONSTRAINED GEOMETRY LIGANDS; CYCLOPENTADIENYL LIGANDS; GENERAL FORMULAS; HALF-SANDWICH; OPTICALLY ACTIVE; P LIGANDS; PHOSPHANE LIGANDS; SYNTHESISED;

LIGANDS;

COORDINATION COMPOUND; PHOSPHORUS DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; ISOMERIZATION; OXIDATION REDUCTION REACTION; RING OPENING; STEREOCHEMISTRY;

EID: 4644240867     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200300934     Document Type: Article

References (89)

1. [1a] S.-I. Murahashi, T. Naota, J. Synth. Org. Chem. Jpn. 1988, 46, 930-956.
2. [1b] T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599-2660.
3. [1c] B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067-2096.
4. [1d] B. M. Trost, Acc. Chem. Res. 2002, 35, 695-705.
5. [1e] V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769.
6. [2a] M. I. Bruce, M. A. Bennett, T. W. Matheson, Comprehensive Organometallic Chemistry (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon Press: Oxford, 1982.
7. [2b] M. I. Bruce, M. A. Bennett, A. F. Hill, Comprehensive Organometallic Chemistry II (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon Press: Oxford, 1995.
8. [2c] U. Kölle, Encyclopedia of Inorganic Chemistry (Ed.: R. King), Wiley Chichester, 1994, 7, 3533-3545.
9. [3a] T. P. Gill, K. R. Mann, Organometallics 1982, 1, 485-488.
10. [3b] B. M. Trost, C. M. Older, Organometallics 2002, 21, 2544-2547.
11. M. O. Albers, D. J. Robinson, A. Shaver, E. Singleton, Organometallics 1986, 5, 2199-2205.
12. C. Slugov, E. Rüba, R. Schmid, K. Kirchner, K. Mereiter, Monatsh. Chem. 2000, 131, 1241-1248.
13. W. Luginbühl, P. Zbinden, P. A. Pittet, T. Armbruster, H. B. Bürgi, A. E. Merbach, A. Ludi, Inorg. Chem. 1991, 30, 2350-2355.
14. [7a] B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. 2002, 114, 1101-1103; Angew. Chem. Int. Ed. 2002, 41, 1059-1162.
15. [7a] B. M. Trost, P. L. Fraisse, Z. T. Ball, Angew. Chem. 2002, 114, 1101-1103; Angew. Chem. Int. Ed. 2002, 41, 1059-1162.
16. [7b] B. M. Trost, H. C. Shen, Angew. Chem. 2001, 113, 2375-2378; Angew. Chem. Int. Ed. 2001, 40, 2313-2317.
17. [7b] B. M. Trost, H. C. Shen, Angew. Chem. 2001, 113, 2375-2378; Angew. Chem. Int. Ed. 2001, 40, 2313-2317.
18. [7c] B. M. Trost, J.-P. Surivet, Angew. Chem. 2001, 113, 1516-1519; Angew. Chem. Int. Ed. 2001, 40, 1468-1472.
19. [7c] B. M. Trost, J.-P. Surivet, Angew. Chem. 2001, 113, 1516-1519; Angew. Chem. Int. Ed. 2001, 40, 1468-1472.
20. [7d] B. M. Trost, A. B. Pinkerton, Angew. Chem. 2000, 112, 368-370; Angew. Chem. Int. Ed. 2000, 39, 360-362.
21. [7d] B. M. Trost, A. B. Pinkerton, Angew. Chem. 2000, 112, 368-370; Angew. Chem. Int. Ed. 2000, 39, 360-362.
22. [7e] B. M. Trost, A. B. Pinkerton, M. Seidel, J. Am. Chem. Soc. 2001, 123, 12466-12476.
23. [7f] B. M. Trost, A. B. Pinkerton, F. D. Toste, M. Sperrle, J. Am. Chem. Soc. 2001, 123, 12504-12509.
24. [7g] B. M. Trost, M. T. Rudd, J. Am. Chem. Soc. 2002, 124, 4178-4179.
25. [7h] B. M. Trost, A. B. Pinkerton, J. Am. Chem. Soc. 1999, 121, 10842-10843.
26. [7i] B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 1999, 121, 9728-9729.
27. [7l] B. M. Trost, R. E. Brown, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 5877-5878.
28. [7m] B. M. Trost, F. D. Toste, H. Sheng, J. Am. Chem. Soc. 2000, 122, 2379-2380.
29. [7n] B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 714-715.
30. [7o] B. M. Trost, A. B. Pinkerton, J. Am. Chem. Soc. 2000, 122, 8081-8082.
31. [7p] B. M. Trost, A. B. Pinkerton, D. Kremzow, J. Am. Chem. Soc. 2000, 122, 12007-12008.
32. [7q] B. M. Trost, J.-P. Surivet, F. D. Toste, J. Am. Chem. Soc. 2001, 123, 2897-2898.
33. [7r] B. M. Trost, M. Machacek, M. J. Schnaderbeck, Org. Lett. 2000, 2, 1761-1764.
34. [7s] B. M. Trost, H. C. Shen, Org. Lett. 2000, 2, 2523-2525.
35. [7t] B. M. Trost, F. D. Toste, Tetrahedron Lett. 1999, 40, 7739-7743.
36. [8a] E. Rüba, W. Simanko, K. Mauthner, K. M. Soldouzi, C. Slugovc, K. Mereiter, R. Schmid, K. Kirchner, Organometallics 1999, 18, 3843-3850.
37. [8b] C. Slugovc, E. Rüba, R. Schimd, K. Kirchner, Organometallics 1999, 18, 4230-4233.
38. [8c] C. M. Standfest-Hauser, K. Mereiter, R. Schmid, K. Kirchner, Dalton Trans. 2003, 11, 2329-2334.
39. [8d] C. M. Standfest-Hauser, K. Mereiter, R. Schmid, K. Kirchner, Organometallics 2002, 21, 4891-4893.
40. [8e] E. Rüba, K. Mereiter, R. Schmid, V. N. Sapunov, K. Kirchner, H. Schottenberger, M. J. Calhorda, L. F. Veiros, Chem. Eur. J. 2002, 8, 3948-3961.
41. [8f] E. Rüba, K. Mereiter, R. Schmid, K. Kirchner, E. Bustelo, M. C. Puerta, P. Valerga, Organometallics 2002, 21, 2912-2920.
42. [8g] E. Becker, C. Slugovc, E. Rüba, C. Standfest-Hauser, K. Mereiter, R. Schmid, K. Kirchner, J. Organomet. Chem. 2002, 649, 55-63.
43. [8h] E. Rüba, K. Mereiter, R. Schmid, K. Kirchner, H. Schottenberger, J. Organomet. Chem. 2001, 637-639, 70-74.
44. [8i] E. Rüba, K. Mereiter, R. Schmid, K. Kirchner, Chem. Commun. 2001, 19, 1996-1997.
45. [8l] K. Mauthner, K. M. Soldouzi, K. Mereiter, R. Schmid, K. Kirchner, Organometallics 1999, 18, 4681-4683.
46. H. Butenschön, Chem. Rev. 2000, 100, 1527-1564.
47. [10a] N. Dodo, Y. Matsushima, M. Uno, K. Onitsuka, S. Takahashi, J. Chem. Soc., Dalton Trans. 2000, 35-41.
48. [10b] Y. Matsushima, N. Komatsuzaki, Y. Ajioka, M. Yamamoto, H. Kikuchi, Y. Takata, N. Dodo, K. Onitsuka, M. Uno, S. Takahashi, Bull. Chem. Soc. Jpn. 2001, 74, 527-537.
49. Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo, S. Takahashi, J. Am. Chem. Soc. 2001, 123, 10405-10406.
50. A. Doppiu, U. Englert, A. Salzer, Inorg. Chim. Acta 2003, 350, 435-441.
51. E. Becker, K. Mereiter, M. Puchberger, R. Schmid, K. Kirchner, A. Doppiu, A. Salzer, Organometallics 2003, 22, 3164-3170.
52. [14a] T. Kauffmann, J. Ennen, H. Lhotak, A. Rensing, F. Steinseifer, A. Woltermann, Angew. Chem. 1980, 92, 328-329; Angew. Chem. Int. Ed. Engl. 1980, 19, 301-302.
53. [14a] T. Kauffmann, J. Ennen, H. Lhotak, A. Rensing, F. Steinseifer, A. Woltermann, Angew. Chem. 1980, 92, 328-329; Angew. Chem. Int. Ed. Engl. 1980, 19, 301-302.
54. [14b] T. Kauffmann, K. Berghus, A. Rensing, Chem. Ber. 1985, 118, 4507-4516.
55. [15a] S. Ciruelos, U. Englert, A. Salzer, C. Bolm, A. Maischak, Organometallics 2000, 19, 2240-2242.
56. [15b] S. Ciruelos, A. Doppiu, U. Englert, A. Salzer, J. Organomet. Chem. 2002, 663, 183-191.
57. [16a] C. F. Wilcox, R. R. Craig, J. Am. Chem. Soc. 1961, 83, 3866-3871.
58. [16b] A. I. D'yachenko, L. G. Menchikov, O. M. Nefedov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1985, 649-651.
59. [17a] B. Rieger, G. Jany, R. Fawzi, M. Steimann, Organometallics 1994, 13, 647-653.
60. [17b] B. Rieger, G. Jany, M. Steimann, R. Fawzi, Z. Naturforsch., Teil B 1994, 49, 451-458.
61. D. C. Brookings, S. A. Harrison, R. J. Whitby, B. Crombie, R. V. H. Jones, Organometallics 2001, 20, 4574-4583.
62. H. C. Kolb, M. S. Van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547.
63. S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315.
64. [21a] E. N. Tsvetkov, N. A. Bondarenko, I. G. Malakhova, M. I. Kabachnik, Synthesis 1986, 198-205.
65. [21b] H. B. Kagan, M. Tahar, J.-C. Fiaud, Tetrahedron Lett. 1991, 32, 5959-5962.
66. [21c] P. Pellon, Tetrahedron Lett. 1992, 33, 4451-4452.
67. [21d] E. Hauptmann, P. J. Fagan, W. Marshall, Organometallics 1999, 18, 2061-2073.
68. In addition to NMR spectroscopic data, the regio- and stereo-chemistry in the ring opening of (S)-1-cyclohexylspiro[2.4]hepta-4,6-diene has also been confirmed by an X-ray structural determination of a metal complex with the derived cyclopentadienylphosphane ligand: U. Englert, personal communication.
69. T. Lumini, D. N. Cox, R. Roulet, K. Schenk, J. Organomet. Chem. 1992, 434, 363-385.
70. D. N. Cox, R. Roulet, J. Chem. Soc., Chem. Commun. 1989, 175-176.
71. I. Lee, F. Dahan, A. Maisonnat, R. Poilblanc, Organometallics 1994, 13, 2743-2750.
72. [26a] S. Otsuka, K. Tani, Synthesis 1991, 665-680.
73. [26b] R. Noyori, Asymmetric Catalysis in Organic Synthesis, Chapter 3, J. Wiley & Sons, New York, 1994.
74. [26c] S. Akutagawa, K. Tani, Catalytic Asymmetric Synthesis, Chapter 3 (Ed.: I. Ojima), Wiley-VCH, New York, 2000.
75. C. Chapuis, M. Barthe, J.-Y. de Saint Laumer, Helv. Chim. Acta 2001, 84, 230-242.
76. For a discussion of the difficulties encountered in catalyzing the isomerisation of allylic alcohols, see: [28a] C. Bianchini, A. Meli, W. Oberhauser, New J. Chem. 2001, 25, 11-12.
77. [28b] R. Uma, C. Crévisy, R. Grée, Chem. Rev. 2003, 103, 27-52.
78. [29a] R. C. van der Drift, E. Bouwman, E. Drent, J. Organomet. Chem. 2002, 650, 1-24.
79. [29b] B. M. Trost, R. J. Kulawiec, J. Am. Chem. Soc. 1993, 115, 2027-2036.
80. [30a] M. Wang, C.-J. Li, Tetrahedron Lett. 2002, 43, 3589-3591.
81. [30b] X.-F. Yang, M. Wang, R. S. Varma, C.-J. Li, Org. Lett. 2003, 5, 657-660.
82. [30c] M. Wang, X.-F. Yang, C.-J. Li, Eur. J. Org. Chem. 2003, 998-1003.
83. J. M. Brown, B. A. Murrer, J. Chem. Soc., Perkin Trans. 2 1982, 489-497.
84. D. P. Riley, R. E. Shumate, J. Org. Chem. 1980, 45, 5187-5193.
85. G. Miao, B. E. Rossiter, J. Org. Chem. 1995, 60, 8424-8427.
86. [34a] A. Bauer, U. Englert, S. Geyser, F. Podewils, A. Salzer, Organometallics 2000, 19, 5471-5476.
87. [34b] A. Salzer, M. Käser, A. Hosang, A. Bauer, U. Effertz, E. Klinkhammer, F. Podewils, Synthetic Methods of Organometallic and Inorganic Chemistry (Eds.: W. A. Herrmann, G. Brauer), Georg Thieme Verlag: Stuttgart, 2000; 9, 45-58.
88. [34c] A. Salzer, A. Bauer, S. Geyser, F. Podewils, Inorg. Synth. 2003, 34, in press.
89. [34d] A. Salzer, F. Podewils, S. Geyser, Eur. Patent. Appl. 110429.8, Int. Patent. Appl. PCT/IB01/00784.