Synthesis of terpene and steroid dimers and trimers having cyclobutadienyl-Co and aromatic tethers

Journal of Organic Chemistry

Volumn 72, Issue 11, 2007, Pages 4213-4219

  Sierra, Miguel A ^a   Torres, M Rosario ^a,c   De La Torre, María C ^b   Álvaro, Elsa ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^c Laboratorio de Difracción de Rayos X   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC TETHERS; STEROID FRAGMENTS; TERPENES; TRIMERS;

ALCOHOLS; DIMERS; KETONES; SYNTHESIS (CHEMICAL);

OLEFINS;

ALCOHOL DERIVATIVE; AROMATIC COMPOUND; BENZENE; CARBON; COBALT DERIVATIVE; CYCLOBUTANE DERIVATIVE; DIMER; KETONE DERIVATIVE; NATURAL PRODUCT; STEROID; TERPENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELIMINATION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

ALKYNES; CYCLOBUTANES; DIMERIZATION; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PROPANOLS; STEREOISOMERISM; STEROIDS; TERPENES;

EID: 34249821664     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0703698     Document Type: Article

References (40)

1. For an overview of this field, see: (a) Fish, R. H.; Jaouen, G. Organometallics 2003, 22, 36.
2. (b) Dagani, R. Chem. Eng. News 2002, 80, 23.
3. (c) Special issue on bioorganometallic chemistry: J. Organomet. Chem. 1999, 589, Issue 1.
4. (a) Tietze, L. F.; Bell, H. P.; Chandrasekhar, S. Angew. Chem., Int. Ed. 2003, 42, 3996.
5. (b) Mehta, G.; Singh, V. Chem. Soc. Rev. 2002, 31, 324.
6. (a) Schreiber, S. L. Science 2000, 287, 1964.
7. (b) Schreiber, S. L. Chem. Eng. News 2003, 81, 51.
8. (c) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46.
9. Sierra, M. A.; Mancheñe, M. J.; Vicente, R.; Gómez-Gallego, M. J. Org. Chem. 2001, 66, 8920.
10. Álvaro, E.; de la Torre, M. C.; Sierra, M. A. Chem. - Eur. J. 2006, 12, 6403.
11. de la Torre, M. C.; Deometrio, A. M.; Álvaro, E.; García, I.; Sierra, A. M. Org. Lett. 2006, 8, 593.
12. (a) Reppe, W.; Schlichting, O.; Klager, K.; Toepel, T. Liebigs Ann. Chem. 1948, 560, 1.
13. (b) Reppe, W.; Schwechendiek, W. J. Liebigs Ann. Chem. 1948, 560, 104.
14. For reviews, see: (c) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
15. (d) Frühauf, H.-W. Chem, Rev. 1997, 97, 523.
16. (e) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
17. (f) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 46.
18. (g) Boese, R.; Sickle, A. P. V.; Vollhardt, K. P. C. Synthesis 1994, 1374.
19. (h) Schore, N. E. Chem. Rev. 1988, 88, 1081.
20. (i) Vollhardt, K. P. C. Angew. Chem. 1984, 96, 525;
21. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
22. (j) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus L., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 741-770.
23. (k) Shore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1129-1162.
24. Pérez, D.; Siesel, B. A.; Malaska, M. J.; David, E.; Vollhardt, K. P. C. Synlett 2000, 306.
25. (a) Johnson, E. P.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1991, 113, 381.
26. (b) Germanas, J.; Aubert, C.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1991, 113, 4006.
27. Eichberg, M. J.; Dorta, R. L.; Grotjahn, D. B.; Lamottke, K.; Schmidt, M.; Vollhardt, K. P. C. J. Am. Chem. Soc. 2001, 113, 9324.
28. Saá, C.; Crotts, D. D.; Hsu, G.; Vollhardt, K. P. C. Synlett 1999, 487.
29. Kaufman, R. J.; Sidhu, R. S. J. Org. Chem. 1982, 47, 4941.
30. Palomo, C.; González, A.; García, J. M.; Landa, C.; Oiarbide, M.; Rodríguez, S.; Lynden, A. Angew. Chem., Int. Ed. 1998, 37, 180.
31. This is congruent with the reported increment of cyclotrimerization/ cyclobutadiene complex ratio upon increasing the reaction temperature. See: Sheppard, G. S.; Vollhardt, K. P. C. J. Org. Chem. 1986, 51, 5496.
32. The aromatic tether of compound 11, the 1,3,5-trisubstituted regioisomer, possesses magnetically equivalent carbons and protons, showing one signal for the three protons and two signals for the six aromatic carbons.
33. (a) Hardesty, J. H.; Koerner, J. B.; Albright, T. A.; Lee, G.-Y. J. Am. Chem. Soc. 1999, 121, 6055.
34. (b) Wakatsuki, Y.; Nomura, O.; Kitaura, K.; Morokuma, K.; Yamazaki, H. J. Am. Chem. Soc. 1983, 105, 1907.
35. Selected recent examples referred to Rh: (a) Funayama, A.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2005, 127, 15354.
36. (b) Terao, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2001, 123, 10407.
37. (c) Terao, Y.; Wakui, H.; Nomoto, N.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236.
38. Peters, R. H.; Crowe, D. F.; Tanabe, M.; Avery, M. A.; Chong, W. K. M. J. Med. Chem. 1987, 30, 646.
39. The lack of reactivity of trimethylsilyl alkynyl carboranes has been recognized; contrary to phenyl alkynyl carboranes that render the cobaltacyclobutadiene derivatives under analogous reaction conditions. Goswami, A.; Nie, Y.; Oeser, T.; Siebert, W. Eur. J. Inorg. Chem. 2006, 566.
40. A nitrogen coordinated cobaltacyclopentadiene has been proposed by Saá et al. to explain regioselectivity in the synthesis of 3,3′-substituted 2,2′-bipyridines: Varela, J. A.; Castedeo, L.; Maestro, M.; Mahía, J.; Saá, C. Chem. - Eur. J. 2001, 7, 5203.