Formation of chiral ionic liquids and imidazol-2-ylidene metal complexes from the proteinogenic aminoacid l-histidine

Journal of Organometallic Chemistry

Volumn 690, Issue 24-25, 2005, Pages 5959-5972

  Hannig, Frithjof ^a   Kehr, Gerald ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Arduengo carbenes; Bio organometallic chemistry; Chiral ionic liquid; Imidazolium salts; Metal complexes

Indexed keywords

AMINO ACIDS; DERIVATIVES; RHODIUM COMPOUNDS;

ARDUENDO-CARBENES; BIO-ORGANOMETALLIC CHEMISTRY; CHIRAL IONIC LIQUIDS; IMIDAZOLIUM SALTS; METAL COMPLEXES;

COMPLEXATION;

EID: 27744554585     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.07.115     Document Type: Article

References (91)

1. L. Xu, W. Chen, and J. Xiao Organometallics 19 2000 1123 1127
2. F. McLachlan, C.J. Mathews, P.J. Smith, and T. Welton Organometallics 22 2003 5350 5357
3. Reviews: T. Welton Chem. Rev. 99 1999 2071 2083
4. R. Sheldon Chem. Commun. 2001 2399 2407
5. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3692
6. P. Wasserscheid Chem. Unserer Zeit 1 2003 52 63
7. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim
8. T. Welton Coord. Chem. Rev. 248 2004 2459 2477
9. W.A. Herrmann, L.J. Gooßen, C. Köcher, and G.R.J. Artus Angew. Chem. 108 1996 2980 2982
10. Angew. Chem., Int. Ed. Engl. 35 1996 2805 2807
11. W.A. Herrmann, and C. Köcher Angew. Chem. 109 1997 2256 2282
12. Angew. Chem., Int. Ed. Engl. 36 1997 2162 2187
13. W.A. Herrmann, L.J. Gooßen, and M. Spiegler Organometallics 17 1998 2162 2168
14. W.A. Herrmann, V.P.W. Böhm, C.W.K. Gstöttmayr, and T. Westkamp J. Organomet. Chem. 585 1999 348 352
15. D.S. McGuinness, and K.J. Cavell Organometallics 18 1999 1596 1606
16. D.S. McGuinnes, and K.J. Cavell Organometallics 19 2000 741 748
17. D. Bourissou, O. Guerret, F.P. Gabbai, and G. Bertrand Chem. Rev. 100 2000 39 91
18. W.A. Herrmann, V.P.W. Böhm, C.W.K. Gstöttmayr, and T. Westkamp J. Organomet. Chem. 595 2000 186 190
19. W.A. Herrmann, V.P.W. Böhm, C.W.K. Gstöttmayr, M. Grosche, C.-P. Reisinger, and T. Westkamp J. Organomet. Chem. 2001 617 618 616-628
20. W.A. Herrmann Angew. Chem. 114 2002 1342 1363
21. Angew. Chem., Int. Ed. Engl. 41 2002 1290 1309
22. W.A. Herrmann, T. Westkamp, and V.P.W. Böhm Adv. Organomet. Chem. 48 2002 1 69
23. J.A. Loch, M. Albrecht, E. Peris, J. Mata, J.W. Faller, and R.H. Crabtree Organometallics 21 2002 700 706
24. S.J. Connon, A.M. Dunne, and S. Blechert Angew. Chem. 114 2002 3989 3993
25. Angew. Chem., Int. Ed. Engl. 41 2002 3835 3838
26. M. Zaja, S.J. Connon, A.M. Dunne, M. Rivard, N. Buschmann, J. Jiricek, and S. Blechert Tetrahedron 59 2003 6545 6558
27. A. Fürstner, G. Seidel, D. Kremzow, and C.W. Lehmann Organometallics 22 2003 907 909
28. J. Howarth, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097 3100
29. P. Wasserscheid, A. Bösmann, and C. Bolm Chem. Commun. 2002 200 201
30. P. Kiełbasiński, M. Albrycht, J. Łuczak, and M. Mikołajczyk Tetrahedron: Asymmetry 13 2002 735 738
31. Y. Ishida, H. Miyauchi, and K. Saigo Chem. Commun. 2002 2240 2241
32. J. Levillain, G. Dubant, I. Abrunhosa, M. Gulea, and A.-C. Gaumont Chem. Commun. 2003 2914 2915
33. W. Bao, Z. Wang, and Y. Li J. Org. Chem. 68 2003 591 593
34. T. Biedroń, and P. Kubisa Polymer Int. 52 2003 1584 1588
35. R.T. Dere, R.R. Pal, P.S. Patil, and M.M. Salunkhe Tetrahedron Lett. 44 2003 5351 5353
36. R.P. Gaisberger, M.H. Fechter, and H. Griengl Tetrahedron: Asymmetry 15 2004 2959 2963
37. M. Berthod, J.-M. Joerger, G. Mignani, M. Vaultier, and M. Lemaire Tetrahedron: Asymmetry 15 2004 2219 2221
38. B. Pégot, G. Vo-Thanh, D. Gori, and A. Loupy Tetrahedron Lett. 45 2004 6425 6428
39. J.M. Fraile, J.I. García, C.I. Herrerías, J.A. Mayoral, O. Reiser, and M. Vaultier Tetrahedron Lett. 45 2004 6765 6768
40. J. Ding, and D.W. Armstrong Chirality 17 2005 281 292
41. S. Lee, Y.J. Zhang, J.Y. Piao, H. Yoon, C.E. Song, J.H. Choi, and J. Hong Chem. Commun. 2003 2624 2625
42. W. Bao, Z. Wang, and Y. Li J. Org. Chem. 68 2003 591 593
43. H. Ma, X. Wan, X. Chen, and Q. Zhou Chin. J. Polym. Sci. 21 2003 265 270
44. M. Tosoni, S. Laschat, and A. Baro Helv. Chim. Acta 87 2004 2742 2749
45. G.V. Thanh, B. Pegot, and A. Poupy Eur. J. Org. Chem. 2004 1112 1116
46. B. Gadenne, P. Hesemann, and J.J.E. Moreau Tetrahedron Lett. 45 2004 8157 8160
47. J.J. Jodry, and K. Mikami Tetrahedron Lett. 45 2004 4429 4431
48. C. Patrascu, C. Sugisaki, C. Mingotaud, J.-D. Marty, Y. Génisson, and N. Lauth-de Viguerie Heterocycles 63 2004 2033 2041
49. J. Ding, T. Welton, and D.W. Armstrong Anal. Chem. 76 2004 6819 6822
50. J. Ding, V. Desikan, X. Han, T.L. Xiao, R. Ding, W.S. Jenks, and D.W. Armstrong Org. Lett. 7 2005 335 337
51. N. Jain, A. Kumar, S. Chauhan, and S.M.S. Chauhan Tetrahedron 61 2005 1015 1060
52. E.J. Kim, S.Y. Ko, and E.K. Dziadulewicz Tetrahedron Lett. 46 2005 631 633
53. K. Fukumoto, M. Yoshizawa, and H. Ohno J. Am. Chem. Soc. 127 2005 2398 2399
54. D. Enders, H. Gielen, G. Raabe, J. Runsink, and J.H. Teles Chem. Ber. 129 1996 1483 1488
55. G. Sini, O. Eisenstein, and R.H. Crabtree Inorg. Chem. 41 2002 602 604
56. V. César, S. Bellemin-Laponnaz, and L.H. Gade Chem. Soc. Rev. 33 2004 619 636
57. H.C. Beyerman, L. Maat, and A. van Zon Recl. Trav. Chim. 91 1972 246 250
58. O. Gerngross Z. Physiol. Chem. 108 1919 50
59. J.B. Jones, and D.W. Hysert Can. J. Chem. 49 1971 3012 3019
60. J.B. Campbell J. Chem. Soc., Perkin Trans. I 1983 1213 1217
61. A.R. Fletcher, J.H. Jones, W.I. Ramage, and A.V. Stachulski J. Chem. Soc., Perkin Trans. 1 1979 2261 2265
62. G.B. Fields, and R.L. Noble Int. J. Peptide Protein Res. 35 1990 161 214
63. See for a comparison: A. Malanda Kimbonguila, S. Boucida, F. Guibé, and A. Loffet Tetrahedron 53 1997 12525 12538
64. G. Erker, and A.A.H. van der Zeijden Angew. Chem. 102 1990 543 545
65. Angew. Chem., Int. Ed. Engl. 29 1990 512 514
66. G. Erker J. Organomet. Chem. 400 1990 185 203
67. G. Erker Pure Appl. Chem. 64 1992 393 401
68. G. Erker, J. Schamberger, A.A.H. van der Zeijden, S. Dehnicke, C. Krüger, R. Goddard, and M. Nolte J. Organomet. Chem. 459 1993 107 115
69. J. Howarth, K. Hanlon, D. Fayne, and P. McCormac Tetrahedron Lett. 38 1997 3097 3100
70. G. Bar, F. Bibi, and A.F. Parsons Synth. Commun. 33 2003 213 222
71. H.M.J. Wang, and I.J.B. Lin Organometallics 17 1998 972 975
72. K.M. Lee, H.M.J. Wang, and I.J.B. Lin J. Chem. Soc., Dalton Trans. 2002 2852 2856
73. A.R. Chianese, X. Li, M.C. Janzen, J.W. Faller, and R.H. Crabtree Organometallics 22 2003 1337 1663
74. X. Hu, Y. Tang, P. Gantzel, and K. Meyer Organometallics 22 2003 612 614
75. D.S. McGuinness, and K.J. Cavell Organometallics 19 2000 741 748
76. J.A. Chamizo, J. Morgado, M. Castro, and S. Bernès Organometallics 21 2002 5428 5432
77. A.A.D. Tulloch, S. Winston, A.A. Danopoulos, G. Eastham, and M.B. Hursthouse Dalton Trans. 2003 699 708
78. A.R. Chianese, X. Li, M.C. Janzen, J.W. Faller, and R.H. Crabtree Organometallics 22 2003 1663 1667
79. P. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, and M. Grätzel Inorg. Chem. 35 1996 1168 1178
80. K.R. Dixon, and A.C. Dixon E.W. Abel F.G. Stone G. Wilkinson R.J. Puddephatt Comprehensive Organometallic Chemistry II vol. 9 1995 Elsevier Oxford 193 223
81. R.S. Simons, P. Custer, C.A. Tessier, and W.J. Youngs Organometallics 22 2003 1979 1982
82. M.J. Doyle, and M.F. Lappert Chem. Commun. 1997 679 680
83. A.C. Chen, L. Ren, A. Decken, and C.M. Crudden Organometallics 19 2000 3459 3461
84. D. Vagedes, G. Erker, and R. Fröhlich J. Organomet. Chem. 641 2002 148 155
85. J. Organomet. Chem. 651 2002 157
86. Programs used: data collection express (Nonius B.V., 1994) and collect (Nonius B.V., 1998), data reduction MolEN (K. Fair, Enraf-Nonius B.V., 1990) and Denzo-SMN Z. Otwinowski, and W. Minor Methods Enzymol. 276 1997 307 326
87. Absorption correction for CCD data sortav: R.H. Blessing Acta Crystallogr., Sect. A 51 1995 33 37
88. R.H. Blessing J. Appl. Crystallogr. 30 1997 421 426
89. Structure solution shelxs-97 G.M. Sheldrick Acta Crystallogr., Sect. A 46 1990 467 473
90. Structure refinement shelxl-97: G.M. Sheldrick, Universität Göttingen, 1997.
91. Graphics schakal: E. Keller, Universität Freiburg, 1997.