Diastereoselective synthesis of the first enantiomerically pure (triazolinylidene)ruthenium(II) and -rhodium(III) chelate complexes

Chemische Berichte

Volumn 130, Issue 9, 1997, Pages 1253-1260

  Enders, Dieter ^a   Gielen, Heike ^a   Raabe, Gerhard ^b   Runsink, Jan ^b   Henrique Teles, J ^b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b BASF SE   (Germany)

Author keywords

(carbene)rhodium complexes; (carbene)ruthenium complexes; Chelate complexes; Chiral carbenes; Chirality

Indexed keywords

EID: 33745395811     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300913     Document Type: Article

References (59)

1. H.-W. Wanzlick, Angew. Client. 1962, 74, 129;
2. Angcn: Client. Int. Ed. Engl. 1962, 1, 75.
3. H.-W. Wanzlick, H.-J. Schönherr, Angew. Client. 1968, 80, 154;
4. Angew. Chcm. Int. Ed Engl. 1968, 7, 141.
5. [3a] K öfele, Angew. Client. 1969, 81, 936;
6. Angen: Cliem. Int. Ed. Engl. 1969, 8, 916. -
7. I3b' K. Öfele, J. Organomct. Client. 1968, 72, P42.
8. [4a] R. J. Sundberg, R. F. Bryan, I. F. Taylor, H. Taube, J. Am. Client. Soc. 1974, 96, 381.
9. [4b] D. W. Macomber, R. D. Rogers, Orgcmometallics 1985, 4, 1485.
10. [4c] M. F. Lappert, y. Organomet. Client. 1988, 358, 185.
11. [4d] A. J. Arduengo III, H. V. R. Dias, J. C. Calabrese, F. Davidson, Organometallics 1993, 12, 3405.
12. [4e] A. J. Arduenso III, S. F. Camper, J. C. Calabrese, F. Davidson, J. Am. Chcm. Soc. 1994, 116, 4391.
13. [4f] K. Öfele, W. A. Herrmann, D. Mihalios, M. Elison, E. Herdtweck, W. Scherer, J. Mink, J. Organomet. Chcm. 1993, 459, 177.
14. [4g] K. Öfele, W. A. Herrmann, D. Mihalios, M. Elison, E. Herdtweck, T. Priermeier, P. Kiprof, ibid. 1995, 498, 1.
15. [4h] N. Kühn, T. Kratz, R. Boese, D. Bläser, ibid. 1994, 470, C8.
16. [4i] H. Schumann, M. Glanz, J. Winterfeld, H. Hemling, N. Kühn, T. Kratz, Chem. Ber. 1994, 727, 2369.
17. [4j] W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Augen: Client. 1995, 707, 2602;
18. Angew. Client. Int. Ed. Engl. 1995. 34, 2317.
19. [4k] W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Client. Eur. J. 1996, 2, 772.
20. [4l] W. A. Herrmann, C. Köcher, L. J. Gooßen, G. R. J. Artus, ibid. 1996. 2, 1627.
21. [4m] H. Kücükbay, B. Cetinkaya, S. Guesmi, P. H. Dixneuf, Organometallics 1996, 75, 2434.
22. [4n] W. A. Herrmann, F. C. Munck, G. R. J. Artus, O. Runte, R. Anwander, ibid. 1997, 76, 682.
23. For a recent review of carbene chemistry, see M. Regitz, Augen: Client. 1996, 70S, 791;
24. Angen: Client. Int. Ed. Engl. 1996, 35, 725.
25. [6a] A w Coleman, P. B. Hitchcock, M. F. Lappert, R. K. Maskell, J. H. Müller, J. Organomet. Cliem. 1983, 250, C9.
26. [6b] A. W. Coleman, P. B. Hitchcock, M. F. Lappert, R. K. Maskell, J. H. Müller, ibid. 1985, 290, 173.
27. D. Enders, H. Gielen, G. Raabe, J. Runsink, J. H. Teles, Client. Ber. 1996, 729, 1483.
28. W. A. Herrmann, L. J. Gooßen, C. Köcher, G. R. J. Artus, Augen: Client. 1996, 108, 2980;
29. Angew. Client, fut. Ed. Engl. 1996, 35, 2805.
30. P. B. Hitchcock, M. F. Lappert, P. L. Pye, S. Thomas, J. Chem. Soc., Dalton Trans. 1979, 1929. -
31. P. B. Hitchcock, M. F. Lappert, P. L. Pye, J. Client. Soc., Client. Commun. 1977, 197.
32. For some recent examples of chiral ruthenium complexes, see
33. [10a] R. Noyori, S. Hashmuchi, Ace. Chcm. Res. 1997, JO, 97.
34. [10b] M. I. Bruee, B. C. Hall, N. N. Zaitseva, B. W. Skelton, A. H. White, J. Organomet. Chcm. 1996, 522, 307.
35. [10c] H. Brunner, R. Oeschey, B. Nuber, J. Client. Soc., Dalton Trans. 1996, 1499.
36. For some recent examples of chiral rhodium complexes, see
37. [11a] M. Ballhorn, M. G. Partridee, R. N. Perutz, M. K. Whittlesey, J. Cliem. Soc.. Cliem. Commun. 1996, 961.
38. [11b] D. Carmona, F. J. Lahoz, L. A. Oro, M. P. Lamata, F. Vicuri, E. San José, Organometallics 1996, 75, 2961.
39. Software used for the presentation: Ball & stick vers. 2.2, A. Falk, N. Müller, G. Schoppel, L.Webb, Linz (Austria), Stafford (Great Britain).
40. [l4c]. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100404. Copies of the data can be obtained free of charge on application to: The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, [Fax: (internat.) +44 (0)1223 336033 deposit@chemcrys.cam.ac.uk
41. [14a] G M Sheldrick in Crystallograpliic Computing 3 (Eds. G. M. Sheldrick, C. Krüger, R. Goddard). Oxford University Press, 1985, p. 175-189.
42. [14b] Xtal 3.2 Reference Manual(Eds. S. R. Hall, H. D. Flack, J. M. Stewart), Universities of Western Australia, Geneva and Maryland. Lamb, Perth, 1992.
43. [l4c] H. D. Flack, Ada Cryst. 1983, A39, 876.
44. [15a] c Lecomte, Y. Dusausoy, J. Protas, J. Tirouflet, A. Dormond, J. Organomet. Clicm. 1974, 73, 67.
45. [15b] K. Stanley, M. C. Baird, J. Am. Chew. Soc. 1975, 97, 6598.
46. [15c] T. E. Sloan, Top. Stereochemistry 1981, 12, 1.
47. [16a] p Morandini, G. Consiclio, V. Lucchini, Organometallics 1985, 4, 1202.
48. [16b] F. Morandini, G. Consialio, G. Ciani, A. Sironi, Inorg. Cliim. Ada 1984, 82, L27.
49. [16cl G. Consiglio, F. Morandini, G. Ciani, A. Sironi, Angm: Clicm. 1983, 95, 322;
50. Angew: Chew. Int. Ed Engl. 1983, 22, 333.
51. For the preparation and further application of triazolium salts, see
52. [17a] D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebcl, S. Brode, Augen. Client. 1995, 107, 1119;
53. Angew. Chem. Int. Eil. Engl. 1995, 34, 1021.
54. [17b] J. H. Teles, J.-P. Melder, K. Ebel, R. Schneider, E. Gehrer, W. Harder, S. Brode, D. Enders, K. Breuer, G. Raabe, Heir. Cliim. Ada 1996, 79, 61 and references cited therein.
55. [17c] D. Enders, K. Breuer, J. H. Teles, Hch: Cliim. Ada 1996, 79, 1217.
56. [17d] D. Enders, K. Breuer, J. H. Teles, Helv. Chim. Ada 1996, 79, 1899.
57. [17c] D. Enders, K. Breuer, J. Runsink, J. H. Teles, Liebigs Ann. 1996, 2019.
58. M. A. Bennet, A. K. Smith, J. Chem. Soc., Dalton Trans. 1974, 233.
59. J. W. Kanc, K. Moseley, P. M. Maitlis, J. Am. Chem. Soc. 1969, 91, 5970.