Ruthenium-catalyzed [3 + 2] intramolecular cycloaddition of alk-5-ynylidenecyclopropanes promoted by the "first-generation" Grubbs carbene complex

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10262-10263

  López, Fernando ^a   Delgado, Alejandro ^a   Rodríguez, J Ramón ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBENE; CYCLOPROPANE DERIVATIVE; RUTHENIUM; SOLVENT; TOLUENE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE;

EID: 4143094838     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0480466     Document Type: Article

References (36)

1. (a) Noyori, R.; Odagi, T.; Takaya, H. J. Am. Chem. Soc. 1970, 92, 5780-5781.
2. (b) Binger, P. Angew. Chem., Int. Ed. Engl. 1972, 11, 433-435.
3. (c) Binger, P.; Schuchardt, U. Angew. Chem., Int. Ed. Engl. 1977, 16, 249-250.
4. For reviews, see: (a) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77-151.
5. (b) Yamago, S.; Nakamura, E. Org. React. 2002, 61, 1-217.
6. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
7. (d) Nakamura, E.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111-129.
8. (a) Lewis, R. T.; Motherwell, W. B.; Shipman, M. J. Chem. Soc.; Chem. Commun. 1988, 948-950.
9. (b) Bapuji, S. A.; Motherwell, W. B.; Shipman, M. Tetrahedron Lett. 1989, 30, 7107-7110.
10. (c) Yamago, S.; Nakamura, E. J. Chem. Soc. Chem. Commun. 1988, 1112-1113.
11. (d) Lautens, M.; Ren, Y.; Delanghe, P. H. M. J. Am. Chem. Soc. 1994, 116, 8821-8822.
12. (e) Lautens, M.; Ren, Y. J. Am. Chem. Soc. 1996, 116, 9597-9605.
13. Delgado, A.; Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2003, 125, 9282-9283.
14. (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
15. (b) Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599-2660.
16. (c) Trost, B. M. Acc. Chem. Res. 2002, 35, 695-705.
17. For other Ru-induced cycloadditions, see: (a) Ura, Y.; Sato, Y.; Shiotsuki, M.; Kondo, T.; Mitsudo, T. J. Mol. Catal. A: Chem. 2004, 209, 35-39.
18. (b) Braña, P.; Gimeno, J.; Sordo, J. A. J. Org. Chem. 2004, 69, 2544-2550.
19. (c) Trost, B. M.; Shen, H. C.; Schulz, T.; Koradin, C.; Schirok, H. Org. Lett. 2003, 5, 4149-4151.
20. For recent reviews on metathesis, see: (a) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923.
21. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
22. (c) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
23. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
24. For ring-closing enyne metathesis: (e) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1-18.
25. (f) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678-693.
26. (g) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
27. For other examples concerning nonmetathetic behavior of Grubbs-type carbenes, see: (a) Alcaide, B.; Almendros, P. Chem. Eur. J. 2003, 9, 1258-1262 and references therein.
28. (b) Mori, M.; Saito, N.; Tanaka, D.; Takimoto, M.; Sato, Y. J. Am. Chem. Soc. 2003, 125, 5606-5607.
29. (c) Quayle, P.; Fengas, D.; Richards, S. Synlett 2003, 1797-1800.
30. (d) Schmidt, B. Angew. Chem., Int. Ed. 2003, 42, 4996-4999.
31. (e) Kitamura, T.; Sato, Y.; Mori, M. Chem. Commun. 2001, 1258-1259.
32. Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, 64, 7202-7207.
33. 1H NMR spectra.
34. See Supporting Information for experimental details.
35. 1H NMR). Increasing the reaction temperature to 110 °C brought the reaction to completion.
36. 31P NMR spectrum of this heated residue showed numerous signals.