Carbonylative and hydrosilylative carbocyclization of 1,5-diynes for the synthesis of cyclic dienones

Organometallics

Volumn 27, Issue 6, 2008, Pages 1342-1344

  Shibata, Takanori ^a   Nakagawa, Naohisa ^a   Ueno, Yasunori ^a   Endo, Kohei ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; COMPLEXATION; CYCLIZATION;

CYCLIC DIENONES; HYDROSILYLATIVE CARBOCYCLIZATION;

RHODIUM COMPOUNDS;

EID: 41749088056     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om7012277     Document Type: Article

References (32)

1. (a) Reviews: Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539.
2. (b) Ojima, I.; Moralee, A. C.; Vassar, V. C. Top. Catal. 2002, 19, 89.
3. (c) Widenhoefer, R. A. Acc. Chem. Res. 2003, 35, 905.
4. (d) Varchi, G.; Ojima, I. Curr. Org. Chem. 2006, 10, 1341.
5. (e) Fujiwara, M.; Ojima, I. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 7.
6. (a) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 6478.
7. (b) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539.
8. (a) Ojima, I.; Donovan, R. J.; Shay, W. R. J. Am. Chem. Soc. 1992, 114, 6580.
9. (b) Ojima, I.; Fracchiolla, D. A.; Donovan, R. J.; Banerji, P. J. Org. Chem. 1994, 59, 7594.
10. (c) Ojima, I.; Kass, D. F.; Zhu, J. Organometallics 1996, 15, 5191.
11. (d) Ojima, I.; Zhu, J.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690.
12. (e) Ojima, I.; Vu, A. T.; McCullagh, J. V.; Kinoshita, A. J. Am. Chem. Soc. 1999, 121, 3230.
13. (f) Ojima, I.; Lee, S.-Y. J. Am. Chem. Soc. 2000, 122, 2385.
14. (g) Ojima, I.; Vu, A. T.; Lee, S.-Y.; McCullagh, J. V.; Moralee, A. C.; Fujiwara, M.; Hoang, T. H. J. Am. Chem. Soc. 2002, 124, 9164.
15. (a) Fukuta, Y.; Matsuda, I.; Itoh, K. Tetrahedron Lett. 1999, 40, 4703.
16. (b) Chakrapani, H.; Liu, C.; Widenhoefer, R. A. Org. Lett. 2003, 5, 157.
17. (c) Park, K. H.; Kim, S. Y.; Son, S. U.; Chung, Y. K. Eur. J. Org. Chem. 2003, 4341.
18. (d) Park, K. H.; Jung, I. C.; Kim, S. Y.; Chung, Y. K. Org. Lett. 2003, 5, 4967.
19. (e) Maerten, E.; Delerue, H.; Queste, M.; Nowicki, A.; Suisse, I.; Agbossou-Niedercorn, F. Tetrahedron: Asymmetry 2004, 15, 3019.
20. (f) Fan, B.-M.; Xie, J.-H.; Li, S.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2007, 46, 1275.
21. (g) Denmark, S. E.; Liu, J. H.-C. J. Am. Chem. Soc. 2007, 129, 3131.
22. (a) Muraoka, T.; Matsuda, I.; Itoh, K. Tetrahedron Lett. 1998, 39, 7325.
23. (b) Muraoka, T.; Matsuda, I.; Itoh, K. Organometallics 2002, 21, 3650.
24. Shibata, T.; Kadowaki, S.; Takagi, K. Organometallics 2004, 23, 4116.
25. (a) Pd- and Pt-catalyzed silylcarbocyclizations were also reported: Widenhoefer, R. A.; DeCarli, M. A. J. Am. Chem. Soc. 1998, 120, 3805.
26. (b) Wang, X.; Chakrapani, H.; Madine, J. W.; Keyerleber, M. A.; Widenhoefer, R. A. J. Org. Chem. 2002, 67, 2778.
27. (c) Uno, T.; Wakayanagi, S.; Sonoda, Y.; Yamamoto, K. Synlett 2003, 1997.
28. (d) Perch, N. S.; Widenhoefer, R. A. J. Am. Chem. Soc. 2004, 126, 6332.
29. Carbonylative carbocyclization of enediynes proceeded under an atmospheric pressure of carbon monoxide, and CO was inserted between two carbons of enediyne termini. In this reaction, the silyl group was not incorporated into the product: (a) Ojima, I.; Lee, S.-Y. J. Am. Chem. Soc. 2000, 122, 2385.
30. (b) Bennacer, B.; Fujiwara, M.; Ojima, I. Org. Lett. 2004, 6, 3589.
31. (c) Bennacer, B.; Fujiwara, M.; Lee, S.-Y.; Ojima, I. J. Am. Chem. Soc. 2005, 127, 17756.
32. When the reaction of diyne la was examined under an atmospheric pressure of argon without CO gas, cyclization did not occur but, rather, hydrosilylation to unsubstituted alkyne moiety proceeded.