Palladium-catalyzed formal cycloaddition of silacyclobutanes with enones: Synthesis of eight-membered cyclic silyl enolates

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2199-2201

  Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 59849101603     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800603z     Document Type: Article

References (34)

1. (a) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
2. (b) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596.
3. (c) Kotha, S.; Brahmachary, E.; Lahiri, K. Eur. J. Org. Chem. 2005, 4741-4767.
4. Sieburth, S. M.; Cunard, N. T. Tetrahedron 1996, 52, 6251-6282.
5. (a) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678-4679.
6. (b) Wender, P. A.; Ihle, N. C.; Correia, C. R. D. J. Am. Chem. Soc. 1988, 110, 5904-5906.
7. (c) Wender, P. A.; Croatt, M. P.; Witulski, B. Tetrahedron 2006, 62, 7505-7511.
8. (a) Keim, W.; Behr, A.; Röper, M. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Ed.; Pergamon: New York, 1982; Vol. 8; pp 371-462.
9. (b) Tenaglia, A.; Brum, P.; Waegell, B. J. Organomet. Chem. 1985, 285, 343-357.
10. (c) Murakami, M.; Itami, K.; Ito, Y. Synlett 1999, 951-953.
11. (a) Carbonaro, A.; Cambisi, F.; Dall'Asta, G. J. Org. Chem. 1971, 36, 1443-1445.
12. (b) Baldenius, K.-U.; tom Dieck, H.; König, W. A.; Icheln, D.; Runge, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 305-307.
13. (c) Lautens, M.; Tam, W.; Lautens, J. C.; Edwards, L. G.; Crudden, C. M.; Smith, A. C. J. Am. Chem. Soc. 1995, 117, 6863-6879.
14. (a) Takeyama, Y.; Nozaki, K.; Matsumoto, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 1461-1466.
15. (b) Hirano, K.; Yorimitsu, H.; Oshima, K Org. Lett. 2006, 8, 483-485.
16. Also see: (c) Hirano, K.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 6094-6095.
17. Other groups have also focused on the synthesis of six-membered rings through metal-mediated formal cycloaddition of silacyclobutanes. (a) Sakurai, H.; Imai, T. Chem. Lett. 1975, 891-894.
18. (b) Agenet, N.; Mirebeau, J.-H.; Petit, M.; Thouvenot, R.; Gandon, V.; Malacria, M.; Aubert, C. Organometallics 2007, 26, 819-830.
19. Transition-metal-catalyzed formal cycloaddition of 1,2-disilacyclobutenes with 1,3-dienes under thermal- or photochemical conditions was known to give 1,4-disila-2,6-cyclooctadienes. (a) Sakurai, H.; Kobayashi, T.; Nakadaira, Y. J. Organomet. Chem. 1978, 162, C43-C47.
20. (b) Jzang, T. T.; Lee, C. Y.; Liu, C. S. Organometallics 1988, 7, 1265-1270.
21. (c) Jzang, T. T.; Liu, C. S. Organometallics 1988, 7, 1271-1277.
22. (d) Huang, C. Y.; Liu, C. S. J. Organomet. Chem. 1989, 373, 353-364.
23. (e) Chiang, H.-J.; Liu, C. S. J. Organomet. Chem. 1992, 438, C9-C12.
24. Synthesis of five-membered cyclic silyl enolates via silylene transfer from silacyclopropane and hydrodisilane to enones was reported. (a) Calad, S. A.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 2046-2047.
25. (b) Okamoto, K.; Hayashi, T. Chem. Lett. 2008, 108-109.
26. Unexpected reactions of enones with the silylene source affording six-membered cyclic silyl enolates. (c) Okamoto, K.; Hayashi, T. Org. Lett. 2007, 9, 5067-5069.
27. Tanaka reported palladium-catalyzed coupling reaction of silacyclobutanes with acid halides in the presence of a suitable base yielding six-membered cyclic silyl enolates. (d) Tanaka, Y.; Yamashita, H.; Tanaka, M. Organometallics 1996, 15, 1524-1526.
28. (e) Chauhan, B. P. S.; Tanaka, Y.; Yamashita, H.; Tanaka, M. Chem. Commun. 1996, 1207-1208.
29. (f) Tanaka, Y.; Yamashita, M. Appl. Organomet. Chem. 2002, 16, 51-54.
30. 3 catalyst system did not catalyze the reaction.
31. Silacyclobutanes were found to undergo oxidative addition to platinum, palladium, and cobalt complexes. (a) Yamashita, H.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8873-8874.
32. (b) Tanaka, Y.; Yamashita, H.; Shimada, S.; Tanaka, M. Organometallics 1997, 16, 3246-3248, and ref 7b.
33. The reaction of 1,1-diphenylsilacyclobutane resulted in the recovery of the starting materials. The fact suggests that the coordination of the carbonyl moiety of enones to the silicon atom of the palladasilacyclopentane would be crucial for the reaction. The bulky substituents on the silicon atom would block out the coordination.
34. The ring-opening byproducts resulting from the reactions with alkyl-substituted enones would be formed through a similar reaction pathway.