Molybdenum-catalyzed ring-closing metathesis of allenynes

Organic Letters

Volumn 7, Issue 18, 2005, Pages 3953-3956

  Murakami, Masahiro ^a   Kadowaki, Sho ^a   Matsuda, Takanori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 24944487677     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514348     Document Type: Article

References (33)

1. Grubbs, R. H., Ed. Handbook of Metathesis; Wiley-VCH: Weinheim, 2003.
2. (a) Katz, T. J.; Sivavec, T. M. J. Am. Chem. Soc. 1985, 107, 737.
3. (b) Maifeld, S. V.; Miller, R. L.; Lee, D. J. Am. Chem. Soc. 2004, 126, 12228.
4. For reviews, see: (c) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127.
5. (d) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
6. (e) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
7. (f) Wallace, D. J. Angew. Chem., Int. Ed. 2005, 44, 1912.
8. (a) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
9. (b) Schrock, R. R. J. Mol. Catal. A 2004, 213, 21.
10. (a) Trnka, T. M.; Morgan, J. P.; Sanford, M. S.; Wilhelm, T. E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546.
11. (b) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
12. (a) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2004, 126, 15074.
13. (b) Castarlenas, R.; Eckert, M.; Dixneuf, P. H. Angew. Chem., Int. Ed. 2005, 44, 2576.
14. (c) Galan, B. R.; Giessert, A. J.; Keister, J. B.; Diver, S. T. J. Am. Chem. Soc. 2005, 127, 5762.
15. (d) Kim, M.; Lee, D. Org. Lett. 2005, 7, 1865.
16. For reviews, see: (e) Poulsen, C. S.; Maden, R. Synthesis 2003, 1.
17. (f) Mori, M. J. Mol. Catal. A 2004, 213, 73.
18. (g) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
19. Ahmed, M.; Arnauld, T.; Barrett, A. G. M.; Braddock, D. C.; Flack, K.; Procopiou, P. A. Org. Lett. 2000, 2, 551.
20. For cycloisomerization and cyclization of allenynes, see: (a) Hashmi, A. S. K. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, p 877.
21. (b) Mandai, T. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, p 925.
22. 2 (12% yield).
23. Intermolecular cross-metathesis of terminal alkynes with allenes has so far failed with the catalysis of 1; the alkynes were completely consumed, whereas the allenes remained unchanged.
24. 2Ru=C=CHPh were used as the catalyst.
25. Mo(VI) vinylidene complexes have not been reported. For a theoretical study, see: Stegmann, R.; Neuhaus, A.; Frenking, G. J. Am. Chem. Soc. 1993, 115, 11930.
26. For vinylidene complexes of Mo in lower oxidation states, see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
27. (b) McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363.
28. (c) Lin, Y.-C. J. Organomet. Chem. 2001, 617-618, 141.
29. (d) Ipaktschi, J.; Mohsseni-Ala, J.; Uhlig, S. Eur. J. Inorg. Chem. 2003, 4313.
30. For a theoretical study on [2 + 2] cycloaddition of Mo alkylidene with alkyne and ring-opening of molybdacyclobutene, see: Sheng, Y.; Wu, Y.-D.; Leszczynski, J. Organometallics 2004, 23, 3189.
31. Such a phenomenon is often observed in Ru-catalyzed metathesis reaction. For a recent example, see ref 5b.
32. Murakami, M.; Matsuda, T. In Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vol. 2, p 727.
33. The stereochemistry was assigned by analogy to a similar reaction. Regás, D.; Afonso, M. M.; Rodríguez, M. L.; Palenzuela, J. A. J. Org. Chem. 2003, 68, 7845.