Formation and utility of oxasilacyclopentenes derived from functionalized alkynes

Journal of the American Chemical Society

Volumn 126, Issue 31, 2004, Pages 9522-9523

  Clark, Timothy B ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALLYL ALCOHOL; CYCLOPENTENE DERIVATIVE; OXASILACYCLOPENTENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; COUPLING FACTOR; DERIVATIZATION; MOLECULAR INTERACTION; PROTEIN ISOLATION; SILYLATION; STEREOCHEMISTRY;

ALDEHYDES; ALKYNES; CYCLIZATION; CYCLOPENTANES; KETONES; ORGANOSILICON COMPOUNDS;

EID: 3543125474     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047498f     Document Type: Article

References (30)

1. Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170-173.
2. Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206.
3. Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621-623.
4. Wipf, P.; Stephenson, C. R. J. Org. Lett. 2003, 5, 2449-2452.
5. Takai, K.; Sakamoto, S.; Isshiki, T. Org. Lett. 2003, 5, 653-655.
6. (a) Huang, W.-S.; Chan, J.; Jamison, T. F. Org. Lett. 2000, 2, 4221-4223.
7. (b) Miller, K. M.; Huang, W.-S.; Jamison, T. F. J. Am. Chem. Soc. 2003, 125, 3442-3443.
8. Mahandru, G. M.; Liu, G.; Montgomery, J. J. Am. Chem. Soc. 2004, 126, 3698-3699.
9. For recent examples of silacyclopropene formation, see: (a) Ando, W.; Shiba, T.; Hidaka, T.; Morihashi, K.; Kikuchi, O. J. Am. Chem. Soc. 1997, 119, 3629-3630.
10. (b) Palmer, W. S.; Woerpel, K. A. Organometallics 1997, 16, 4824-4827.
11. Seyferth, D.; Vick, S. C.; Shannon, M. L. Organometallics 1984, 3, 1897-1905.
12. For reviews of C-Si bond oxidation, see: (a) Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI: Greenwich, CT, 1996; Vol. 3, pp 1-62.
13. (b) Fleming, I. Chemtracts-Org. Chem. 1996, 9, 1-64.
14. (c) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662.
15. Ćiraković, J.; Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370-9371.
16. 4-catalyzed silacyclopropenation provides intermediates that are difficult to isolate, thermal silacyclopropenation was used to characterize products. Details are provided as Supporting Information.
17. To date, only one other example of a silacyclopropene generated from a terminal alkyne has been reported, see: Belzner, J.; Ihmels, H. Tetrahedron Lett. 1993, 34, 6541-6544.
18. Siloles or disilacyclohexadienes were typically observed in the silacyclopropenation of terminal alkynes. For examples, see: (a) Seyferth, D.; Shannon, M. L.; Vick, S. C.; Lim, T. F. O. Organometallics 1985, 4, 57-62.
19. (b) Tanaka, Y.; Yamashita, H.; Tanaka, M. Organometallics 1995, 14, 530-541.
20. Calculations of the thermodynamic energies of silacyclopropenes and silacyclopropanes suggest ring strain is decreased in silacyclopropenes: (a) Gordon, M. S. J. Am. Chem. Soc. 1980, 102, 7419-7422.
21. (b) Coller, A.; Heydt, H.; Clark, T. J. Org. Chem. 1996, 61, 5840-5846.
22. Formamides and α,β-unsaturated aldehydes could also be inserted.
23. Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949-957.
24. (a) References 2 and 5.
25. (b) Takai, K.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1990, 55, 1707-1708.
26. (c) Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981.
27. (d) Takai, K.; Sakogawa, K.; Kataoka, Y.; Oshima, K.; Utimoto, K. Org. Synth. 1995, 72, 180-188.
28. Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 6706-6707.
29. Fehr, C. Angew. Chem., Int. Ed. 1998, 37, 2407-2409.
30. Details are provided as Supporting Information.