Introduction of organometallic fragments into α-amino acids by reactions of α-bromoglycine derivatives with anionic organotransition-metal compounds

Chemische Berichte

Volumn 130, Issue 2, 1997, Pages 171-177

  Kayser, Bernd ^a   Polborn, Kurt ^a   Steglich, Wolfgang ^a   Beck, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Amino acids; Chromium; Iron; Transition metal labeled a amino acids; Tungsten; Bromoglycine derivatives

Indexed keywords

EID: 0001237021     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300206     Document Type: Article

References (66)

1. M. Maürus/B. Aechter, W. HofTmüller, K. Polborn, W. Beck, Z. Anorg. Allg. Client., in press.
2. X-ray diffraction.
3. [3a] G jaouen A. Vessiéres, I. S. Butler, Ace. Chcm. Rcs. 1993, 26, 361-369.
4. [3b] M. Salmain, M. Gunn, A. Gorfti, S. Top, G. Japuen, Bioconjugate Chem. 1993, 4, 425-433.
5. [3c] A. Gorfti, M. Salmain, G. Jaouen, M. J. McGlinchey, A. Bennouna, A. Mousser, Organomelallics 1996, 75, 142-151.
6. [3d] A. J. Gleichmann, J. M. Wolff, W. S. Sheldrick, J. Chem. Soc., Dalton Trans. 1995, 1549-1554.
7. [3e] J. M. Wolff, A. J. Gleichmann, W. S. Sheldrick, J. Inorg. Biocliem. 1995, 59, 219.
8. [3f] M R. Krämer, Angew. Chcm. 1996,10S, 1287-1289;
9. Angew. Chem. Int. Eil. Engl. 1996,55, 1197-1199.
10. [3g] M. Schweiger, T. Ederer, K. Sünkel, W. Beck, J. Organomet. Chem., in press.
11. [4a] G. R. Stephenson, Studies in Natural Products Chemistry, Eisevier Science B. V., 1995, vol. 16, p. 395.
12. [4b] K. Schlögl, Monatsh. Chem. 1957, 88, 601-621.
13. [4c] J.-C. Brunei, E. Cuingnet, H. Gras, P. Marcinical, A. Mocz, C. Sergheraert, A. Tartar, J. Organomet. Chem. 1981,276, 73-77.
14. [4d] A. J. Pearson, P. R. Bruhn, F. Gouzoules, S.-Han Lee, J. Chem. Soc., Chem. Commun. 1989, 659-661.
15. [4e] A. J. Pearson, P. R. Bruhn, J. Org. Chem. 1991, 56, 7092-7097.
16. [4f] W. Beck, R. Krämer, Angew. Chem. 1991, 103, 1492-1493;
17. Angew. Chcm. Int. Ed. Engl. 1991, 30, 1467-1469.
18. [4g] M. J. Dünn, R. F. W. Jackson, G. R. Stephenson, Synlett 1992, 905-906.
19. [4h] J. Barker, S. L. Cook, M. L. Lasterra-Sänchez, S. E. Thomas, Inorg. Chim. Acta 1994,220, 137-143.
20. [5a] Q Sergheraert, A. Tartar, J. Organomet. Chem. 1982, 240, 163-168.
21. [5b] C. Sergheraert, J.-C. Brunei, A. Tartar, J. Chem. Soc., Chem. Commun. 1982, 1417-1418.
22. [5c] W. S. Sheldrick, A. J. Gleichmann, J. Organomet. Chem. 1994,470, 183-187.
23. [5d] R. M. Moriarty, Yi-Yin Ku, U. S. Gill, J. Chcm. Soc.. Chem. Commun. 1987, 1837-1838.
24. [6a] p Rose-Munch, K. Aniss, Tetrahedron Lett. 1990, 31, 6351-6354.
25. [6b] F. Rose-Munch, K. Aniss, E. Rose, J. Organomet. Chem. 1990, 385, C1-C3.
26. [6c] F. Rose-Munch, K. Aniss, E. Rose, J. Vaisserman, J. Organomet. Chem. 1991, 415, 223-255.
27. [6d] M. Chaari, J.-P. Lavergne, Ph. Viallefonl, Synth. Commun. 1989, 19, 1211-1216.
28. [6e] M. Chaari, A. Jenhi, J.-P. Lavergne, Ph. Viallefonl, J. Organomet. Chem. 1991, 401, C10-C13.
29. [6f] M. Chaari, A. Jenhi, J.-P. Lavergne, Ph. Viallefont, Tetrahedron 1991, 47, 4619-4630.
30. W. Beck, B. Niemer, M. Wieser, Angew. Chem. 1993, 705, 969-996;
31. Angew. Chem. Int. Ed. Engl. 1993, 32, 923, and literature ciled Hierein.
32. [8a] R Kober w Steglich, Licbigs Ann. Chem. 1983, 599-609.
33. [8b] R. Kober, K. Papadopoulos, W. Miliz, D. Enders, W. Sieglich, Tetrahedron 1985, 41, 1693-1701.
34. [8c] P. Münsler, W. Sieglich, Synthesis 1987, 223-225.
35. [8d] G. Apitz, M. Jäger, S. Jaroch, S. Kralzel, L. Schäffeler, W. Sieglich, Tetrahedron 1993, 49, 8223-8232. -
36. T. Breischneider, W. Miliz, P. Münsler, W. Sieglich, Tetrahedron 1988, 44, 5403-5414.
37. [8e] V. A. Burgess, C. J. Easlon, M. P. Hay, P. J. Sleel, Aust. J. Chem. 1988, 41, 701-710.
38. [8f] S. Jaroch, T. Schwarz, W. Sieglich, P. Zistler, Angew. Chem. 1993, 705, 1803-1805;
39. Angew. Chem. Int. Ed. Engl. 1993,32, 1771.
40. [9a] C. R. Hauser, T. A. Mashburn, J. Org. Cliem. 1961, 26, 1795-1800.
41. [9b] P. Braunstein, T. M. Gomes Carneiro, D. Matt, J. Organoinet. Client. 1989,567, 117-132.
42. [10a] L. S. Liebeskind, M. E. Welker, R. W. Fengl, J. Am. Client. Soc. 1986,108, 6328-6343.
43. [10a] S. G. Davies, AIdrichim. Acta 1990, 23, 31 and literature cited therein.
44. [10c] S. G. Davies, A. E. Derome, J. P. McNally, J. Am. Client. Soc. 1991, 113, 2854-2861.
45. [10d] J. Breimair, M. VVieser, B. Wagner, K. Polborn, W. Beck, J. Organomet. Cliem. 1991, 421, 55-64.
46. [11a] C. G. Kreiter, Angew. Cliem. 1968, 80, 402;
47. Angew. Cliem. Int. Ed. Engl. 1968, 7, 390.
48. [11b] C. P. Casey, W. R. Brunsvold, J. Organomet. Cliem. 1976, 118, 309-323.
49. [11c] C. P. Casey, R. L. Andersen, J. Am. Client. Soc. 1974, 96, 1230-1231.
50. [11d] J. Breimair, T. Weidmann, B. Wagner, W. Beck, Client. Ber. 1991,724,2431-2434.
51. [12) [12a] A. N. Nesmeyanov, N. A. Ustynyuk, L. G. Makarova, S. André, J. Organomet. Client. 1978, 154, 45-63.
52. [12b] A. N. Nesmeyanov, N. A. Ustynyuk, L. N. Novikova, T. N. Rybina, J. Organomet. Cliem. 1980, 184, 63-75.
53. [12c] A. Ceccon, A. Gambaro, G. Agostini, A. Venzo, J. Organomet. Chcin. 1981, 277, 79-89.
54. [12d] A. Ceccon, A. Gambaro, A. Venzo, J. Organomet. Client. 1984, 275, 209-222.
55. [12e] J. Breimair, M. Wieser, W. Beck, J. Organomet. C/iem. 1992, 441, 429-439.
56. A. Jenhi, J. P. Lavergne, Ph. Viallefont, J. Organomet. Client. 1991, 401, C14-C16.
57. [14a] G Bashiardes, S. G. Davies, Tetrahedron Lett. 1988, 29, 6509-6512.
58. [14b] G. Bashiardes, S. P. Collingwood, S. G. Davies. S. C. Preston, J. Organomet. Chem. 1989, 364, C29-C32.
59. [14c] S. P. Collingwood, S. G. Davies, S. C. Preston, Tetrahedron Lett. 1990, 31, 4067-4068.
60. W. Steglich, M. Jäger, S. Jaroch, P. Zistler, Pure Appl. Chem. 1994, 66, 2167-2170.
61. J. P. Bibler, A. Wojicki, Inorg.Chem. 1966, 5, 889-892.
62. E o. Fischer, A. Maasböl, Chem. Ber. 1967, 700, 2445-2456.
63. [17b] E. O. Fischer, U. Schubert, W. Kleine, H. Fischer, Inorg. Synth. 1979, 19, 164-172.
64. [18a] T E Bitterwolf, R. Herzog, P. D. Roîkswold, J. Organomet. Chem. 1987, 320, 197-209.
65. [18b] S. Top, G. Jaouen, J. Organomet. Chem. 1979, 182, 381-392.
66. Further details of the crystal structure determination are available from Fachinformationszentrum Karlsruhe, D-76344 Eggenstein-Leopoldshafen (Germany), on quoting the depository number CSD-405792.