A simple approach toward enantiomerically pure fischer carbene complexes of chromium and molybdenum: Chiral modification of the metal fragment

Organometallics

Volumn 22, Issue 8, 2003, Pages 1756-1760

  Barluenga, José ^a   Muñiz, Kilian ^a,b   Tomás, Miguel ^a   Ballesteros, Alfredo ^a   García Granda, Santiago ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; CHROMIUM COMPOUNDS; FISCHER-TROPSCH SYNTHESIS; FUNCTIONALLY GRADED MATERIALS; ION EXCHANGE; ISOMERIZATION; MOLYBDENUM COMPOUNDS; STOICHIOMETRY;

CHIRAL MODIFICATION; FISCHER CARBENE COMPLEXES; THERMAL EXCHANGE REACTION;

ORGANOMETALLICS;

EID: 0038682027     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0210560     Document Type: Article

References (63)

1. Transition Metals For Organic Chemistry: Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
2. (a) Zaragoza-Dörwald, F. Metal Carbenes in Organic Synthesis; Wiley-VCH: Weinheim Germany, 1999.
3. (b) Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, F. R.; Schubert U.; Weiss K. Transition Metal Carbene Complexes. VCH: Weinheim, Germany, 1983.
4. For recent reviews, see: (a) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: New York, 1995; Vol. 12, p. 469.
5. (b) Barluenga, J.; Flórez, J.; Fañanas, F. J. J. Organomet. Chem. 2001, 624, 5.
6. (c) de Meijere, A.; Schirmer, H.; Duetsch, M. Angew. Chem., Int. Ed. 2000, 39, 3964.
7. (d) Sierra M. A. Chem. Rev. 2000, 100, 3591.
8. (e) Aumann, R. Eur. J. Org. Chem. 2000, 17.
9. (f) Herndon, J. W. Tetrahedron 2000, 56, 1257.
10. For selected recent contributions in this area, see for instance: (a) Bao, J.; Wulff, W. D.; Dominy, J. B.; Fumo, M. J.; Grant, E. B.; Rob, A. C.; Whitcomb, M. C.; Yeung, S.-M.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 3392.
11. (b) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182.
12. (c) Iwasawa, N., Shido M.; Kusama, H. J. Am. Chem. Soc. 2001, 123, 5814.
13. (d) Miura T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
14. Selected recent contributions from our laboratory: (a) Barluenga, J.; López, L. A.; Löber, O.; Tomás, M.; García-Granda, S.; Alvarez-Rúa C.; Borge, J. Angew. Chem. Int. Ed. 2001, 40, 3392.
15. (b) Barluenga, J.; Aznar, F.; Palomero, M. A. Angew. Chem., Int. Ed. 2000, 39, 4346.
16. (c) Barluenga, J.; Aznar, A.; Gutiérrez, I.; Martín, A.; García-Granda, S.; Llorca-Baragaño, M. A. J. Am. Chem. Soc. 2000, 122, 1314.
17. (d) Barluenga, J.; Rodríguez, F.; Fañnás, F. J.; Rubio, E. Angew. Chem., Int. Ed. 1999, 38, 3084.
18. (e) Barluenga, J.; Ballesteros, A.; Santamaría, J.; Bernardo de la Rúa, R.; Rubio, E.; Tomás, M. J. Am. Chem. Soc. 2000, 122, 12874.
19. (a) Wulff, W. D. Organometallics 1998, 17, 3116.
20. (b) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
21. (a) Barluenga, J.; Montserrat, J. M.; Flörez, J.; García-Granda, S.; Martín, E. Angew. Chem. Int., Ed. Engl., 1994, 33, 1392.
22. (b) Rahm, A.; Rheingold, A. L; Wulff, W. D. Tetrahedron 2000, 56, 4951.
23. (c) Hsung, R. P.; Wulff, W. D.; Chamberlin, S.; Liu, Y.; Liu, R.-Y.; Wang, H,; Quinn, J. F.; Wang, S. L. B.; Rheingold, A. L. Synthesis 2001, 200.
24. (d) Barluenga, J.; Fernández-Rodríguez, M. A.; Aguilar E.; Fernández-Marí, F.; Salinas, A.; Olano, B. Chem. Eur. J. 2001, 7, 3533.
25. (e) Merino, I.; Laxmi, S.; Flórez, J.; Barluenga, J.; Ezquerra, J.; Pedregal, C. J. Org. Chem. 2002, 67, 648.
26. (f) Dótz, K. H.; Stinner, C.; Nieger, M. J. Chem. Soc., Chem. Commun. 1995, 2535.
27. (g) Hegedus, L. S.; Schwindt, M. A.; De Lombaert, S.; Imwinkelried, R. J. Am. Chem. Soc. 1990, 112, 2264.
28. (h) Licandro, E.; Maiorana, S.; Capella, L.; Manzotti, R.; Papagni, A.; Vandoni, B.; Albinati, A.; Chuang, S. H.; Hwu, J.-R. Organometallics 2001, 20, 485.
29. For chiral boroxycarbene complexes, see: (a) Barluenga, J.; Rodríguez, F.; Vadecard, J.; Bendix, M.; Fañanás, F. J.; López-Ortiz, F.; Rodríguez, M. A. J. Am. Chem. Soc. 1999, 121, 8776.
30. (b) Barluenga, J.; Fañanás, F. J. Tetrahedron 2000, 56, 4597.
31. (a) Janes, E.; Dötz, K. H. J. Organomed. Chem. 2001, 622, 251.
32. (b) Dötz, K. H.; Jákel, C.; Haase, W.-C. J. Organomet. Chem. 2001, 617-618, 119.
33. (c) Dötz, K. H.; Ehlenz, R. Chem. Eur. J. 1997, 3, 1751.
34. (a) Vorogushin, A. V.; Wulff, W. D.; Hansen, H.-J. J. Am. Chem. Soc. 2002, 124, 6512.
35. (b) Hsung, R. P.; Wulff, W. D.; Challener, C. A. Synthesis 1996, 773.
36. (c) Dötz, K. H.; Tomuschat, P.; Nieger, M. Chem. Ber./Recl. 1997, 130, 1605.
37. (d) Herrmann, R.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1982, 21, 788.
38. Cooke, M. D.; Fisher, E. O. J. Organomet. Chem. 1973, 56, 279.
39. For the replacement of two carbonyl ligands with 1.2-bis-(diphenylphosphino)ethane on chromium Fischer carbene complexes, see Arrieta, A.; Cossio, F. P.; Fernández, I.; Gómez-Gallego, M.; Lecea, B.; Mancheño, M. J.; Sierra, M. A. J. Am. Chem. Soc. 2000, 122, 11509.
40. (a) Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2953.
41. (b) Tolman, C. A. Chem. Rev. 1977, 77, 313.
42. (a) Cunningham, A. F., Jr.; Kündig, E. P. J. Org. Chem. 1988, 53, 1823.
43. (b) Kündig, E. P.; Bourdin, B.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1856.
44. (c) Kündig, E. P.; Saudan, C. M.; Bernadinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1219.
45. (d) Kündig, E. P.; Saudan, C. M.; Viton, F. Adv. Synth. Catal. 2001, 343, 51
46. (e) Kündig, E. P.; Saudan, C. M.; Alezra, V.; Viton, F.; Bernardinelli, G. Angew. Chem., Int. Ed. 2001, 40, 4481.
47. Muniz Fernandez, K. Diploma Thesis, Universidad de Oviedo/Universität Hannover, 1996.
48. This stability is noteworthy and has to be attributed to the introduction of the diphosphite ligand. The parent pentacarbonylmolybdenum complexes are known tobe notoriously unstable; see; Harvey, D. F.; Brown, M. F. Tetrahedron Lett. 1990, 31, 2529.
49. 2}, see: Powell, J.; Gregg, M. R.; Kuksis, A.; May, C. J.; Smith, S. J. Organometallics 1989, 8, 2918.
50. 31P NMR and IR spectra.
51. (a) Such an isomerization has been described for certain tungsten carbene complexes bearing bis-phosphine ligands. However, these complexes do not represent the classical electronic structures of Fischer carbene complexes; see: Schenk, W. A.; Kümmerle, D.; Burschka, C. J. Organomet. Chem. 1988, 349, 183.
52. (b) Heating fac-3 in the absence of carbon monoxide resulted in slow decomposition
53. Fischer, H.; Fischer, E. O.; Werner, H. J. Organomet. Chem. 1974, 73, 331.
54. Barluenga, J.; Muñiz, K.; Ballesteros, A.; Martínez, S.; Toḿs, M. ARKIVOC 2002, 3 (Part V), 110.
55. Fischer, E. O.; Maasböl, A. Chem. Ber. 1967, 100, 2445.
56. (a) Lehman, M. S.; Larsen, F. K. Acta Crystallogr., Sect. A 1974, 30, 580.
57. (b) Grant, D. F.; Gabe, E. J. J. Appl. Crystallogr. 1978, 11, 114.
58. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; García-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF Program System; Technical Report of the Crystallographic Laboratory; University of Nijimegen, Nijimegen, The Netherlands, 1992.
59. Sheldrick, G. M. SHELXL-93. In Crystallographic Computing 6; Flack, H. D., Parkanyi, P., Simon, K., Eds.; IUCr/Oxford University Press: Oxford, U.K., 1993.
60. Parkin, S.; Moezzi, B.; Hope, H. J. Appl. Crystallogr. 1995, 28, 53.
61. International Tables for X-ray Crystallography; Kynoch Press: Birmingham, U.K., 1974; Vol. IV. (present distributor: Kluwer Academic Publishers, Dordrecht, The Netherlands).
62. Spek, A. L. PLATON, a Multipurpose Crystallographic Tool; Ultracht University, Utrecht, The Netherlands, 2000.
63. Nardelli, M. Comput. Chem. 1983, 7, 95.