An efficient synthesis of unsymmetrical 1,1-bis (silyl)ethenes

Synthesis

Volumn , Issue 8, 2006, Pages 1370-1374

  Hreczycho, Grzegorz ^a   Pawluć, Piotr ^a   Marciniec, Bogdan ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

Amino alcohol; Grignard reactions; Organometallic reagents; Silylative coupling; Vinylsilanes

Indexed keywords

ALCOHOLS; CATALYSIS; DERIVATIVES; HYDRIDES; RUTHENIUM; SILICON; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

AMINO ALCOHOL; GRIGNARD REACTIONS; ORGANOMETALLIC REAGENTS; SILYLATIVE COUPLING; VINYLSILANES;

AROMATIC COMPOUNDS;

1 (ETHOXYDIMETHYLSILYL) 1 (ORGANYLDIMETHYLSILYL)ETHENE DERIVATIVE; 1 AZA 1,2,2,4,4 PENTAMETHYL 3 METHYLENE 5 OXA 2,4 DISILACYCLOHEPTANE; 1,1 BIS(SILYL)ETHENE DERIVATIVE; ETHYLAMINE; ETHYLENE; HEPTANE DERIVATIVE; N METHYL N (DIMETHYLVINYLSILYL) 2 (DIMETHYLVINYLSILYLOXY)ETHANAMINE; RUTHENIUM COMPLEX; SILICON; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; ATOM; CATALYSIS; CYCLIZATION; GRIGNARD REACTION; METHODOLOGY; SYNTHESIS;

EID: 33646234734     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926406     Document Type: Article

References (29)

1. (a) Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
2. (b) The Chemistry of Organosilicon Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1988, Chap. 3.
3. (c) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063.
4. (a) Padwa, A.; MacDonald, J. G. J. Org. Chem. 1983, 48, 3189.
5. (b) Hodgson, D. M.; Comina, P. J.; Drew, M. G. B. J. Chem. Soc., Perkin Trans. 1 1997, 2279.
6. (c) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 11109.
7. (d) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Commun. 2002, 114.
8. (a) Narasaka, K.; Saito, N.; Hayashi, Y.; Ichida, H. Chem. Lett. 1990, 1411.
9. (b) Fleming, I.; Ghosh, U. J. Chem. Soc., Perkin Trans. 1 1994, 257.
10. (c) Inoue, A.; Kondo, J.; Shinokubo, H.; Oshima, K. Chem. Lett. 2001, 956.
11. (d) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 2002, 43, 2399.
12. (a) Kondo, J.; Inoue, A.; Shinokubo, H.; Oshima, K. Chem. Eur. J. 2002, 8, 1730.
13. (b) Jones, P. R.; Bates, T. F. J. Am. Chem. Soc. 1987, 109, 913.
14. (c) Miura, K.; Hondo, T.; Okajima, S.; Nakagawa, T.; Takahashi, T.; Hosomi, A. J. Org. Chem. 2002, 67, 6082.
15. (d) Ohmiya, H.; Yorimitsu, H.; Oshima, K. Angew. Chem. Int. Ed. 2005, 44, 3488.
16. For reviews, see: (a) Marciniec, B.; Pietraszuk, C.; Kownacki, I.; Zaidlewicz, M. Vinyl and Aryl Silicon, Germanium, and Boron Compounds, In Comprehensive Organic Functional Group Transformations II, Vol. 2; Katritzky, A. R.; Taylor, R. J. K., Eds.; Elsevier: Oxford, 2005, 941-1023.
17. (b) Marciniec, B.; Pietraszuk, C. Curr. Org. Chem. 2003, 7, 691.
18. (c) Marciniec, B.; Pietraszuk, C. In Topics in Organometallic Chemistry, Synthesis of Silicon Derivatives with Ruthenium Catalysts; Dixneuf, P., Ed.; Springer: Berlin, 2004, 197-248.
19. (a) Wakatsuki, Y.; Yamazaki, H.; Nakano, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1991, 703.
20. (b) Marciniec, B.; Pietraszuk, C. J. Chem. Soc., Chem. Commun. 1995, 2003.
21. (c) Marciniec, B.; Pietraszuk, C. Organometallics 1997, 16, 4320.
22. (a) Marciniec, B.; Lewandowski, M. Tetrahedron Lett. 1997, 38, 3777.
23. (b) Mise, T.; Takaguchi, Y.; Urnemiya, T.; Shimizu, S.; Wakatsuki, Y. Chem. Commun. 1998, 699.
24. (c) Marciniec, B.; Lewandowski, M.; Bijpost, E.; Małecka, E.; Kubicki, M.; Walczuk-Guściora, E. Organometallics 1999, 20, 3968.
25. (d) Marciniec, B.; Matecka, E. Macromol. Symp. 2001, 174, 137.
26. (e) Majchrzak, M.; Marciniec, B.; Kubicki, M.; Pawelczyk, A. Organometallics 2005, 24, 3731.
27. (a) Pawluć, P.; Marciniec, B.; Hreczycho, G.; Gaczewska, B.; Itami, Y. J. Org. Chem. 2005, 70, 370.
28. (b) Pawluć, P.; Hreczycho, G.; Marciniec, B. Synlett 2005, 1105.
29. Yi, C. S.; Lee, D. W.; Chen, Y. Organometallics 1999, 18, 2043.