Regio- and stereoselective enyne cross metathesis of silylated internal alkynes

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10242-10243

  Kim, Mansuk ^a   Park, Sangho ^a   Maifeld, Sarah V ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; FUNCTIONAL GROUP; SILANE DERIVATIVE; SILYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENYNE CROSS METATHESIS; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY;

ALKENES; ALKYNES; ORGANOSILICON COMPOUNDS; STEREOISOMERISM;

EID: 4143150671     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0465909     Document Type: Article

References (27)

1. Reviews: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
2. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013.
3. (c) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592.
4. Review: Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
5. Reviews: (a) Giessert, A. J.; Diver, S. T. Chem. Rev. 2004, 104, 1317.
6. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
7. (c) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
8. Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465.
9. (a) Konishita, A.; Sakakibura, N.; Mori. M. J. Am. Chem. Soc. 1997, 119, 12388.
10. (b) Smulik, J.; A.; Diver, S. T. J. Org. Chem. 2000, 65, 1788.
11. Stragies, R.; Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2518.
12. EYCM reaction of silylated internal alkyne with allyl acetate afforded 10% yield of CM product. Kotha, S.; Halder, S.; Brahmachary, E.; Ganesh, T. Synlett 2000, 853.
13. (a) Antras, F.; Ahmar, M.; Cazes, B. Tetrahedron Lett. 2001, 42, 8157.
14. (b) Trost, B. M.; Machacek, M.; Schnaderbeck, M. J. Org. Lett. 2000, 2, 1761.
15. (c) Wender, P. A.; Deschamps, N. M.; Williams, T. J. Angew. Chem., Int. Ed. 2004, 43, 3076.
16. For RCM reaction with alkynylsilanes, see: Miller, R. L.; Maifeld, S. V.; Lee, D. Org. Lett. 2004, 6, 2773.
17. EYCM of 3a with allyltrimethylsilane gave only 5a without any allyltrimethylsilane-crossed product. For EYCM of allyltrimethylsilane and trimethyl- and triphenysilylacetylene, see: ref 4 and Lee, H.-Y.; Kim, B. G.; Snapper, M. L. Org. Lett. 2003, 5, 1855.
18. The stereochemistry of 4i was assigned based on the coupling constant (J = 15.8 Hz) of the desilylated compound. See the Supporting Information.
19. Reaction of 3a with ethylene provided 5a in quantitative yield.
20. Tonogaki, K.; Mori, M. Tetrahedron Lett. 2002, 43, 2235.
21. Arisawa, M.; Terada, Y.; Nakagawa, M.; Nishida, A. Angew. Chem., Int. Ed. 2002, 41, 4732 and references therein.
22. For a double bond-chelate, see: (a) Tallarico, J. A.; Bonitatebus, P. J., Jr.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157.
23. (b) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845. For an oxygen-chelate, see: Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
24. (b) Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845. For an oxygen-chelate, see: Engelhardt, F. C.; Schmitt, M. J.; Taylor, R. E. Org. Lett. 2001, 3, 2209.
25. (a) For a theoretical study of the ring-opening of metallacyclobutene and cyclobutene, see: Sheng, Y.; Wu, Y.-D.; Leszczynski, J. Organometallics 2004, 3189.
26. (b) Lee, P. S.; Zhang, X.; Houk, K. N. J. Am. Chem. Soc. 2003, 125, 5072.
27. For similar examples, see: Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.