Chemoselective addition of organometallics to oxime ethers

Journal of Organometallic Chemistry

Volumn 692, Issue 10, 2007, Pages 1924-1927

  Tavakol, Hossein ^a   Zakery, Saedeh ^a   Heydari, Akbar ^b  

^a UNIVERSITY OF ZABOL   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Chemoselective reactions; Lithiumperchlorate; Multicomponent reaction; Organosilane; Organotin; Oximes

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; CONDENSATION REACTIONS; ETHERS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVE ADDITION; HYDROXYLAMINES; LITHIUMPERCHLORATE; MULTICOMPONENT REACTION; OXIME ETHERS;

ORGANOMETALLICS;

EID: 33947578541     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.12.038     Document Type: Article

References (21)

1. Tietze L.F. Chem. Rev. 96 (1996) 115
2. Bienayme H., Hulme C., Oddon G., and Schmitt P. Chem. Eur. J. 6 (2000) 321
3. Doemling A., and Ugi I. Angew. Chem. Int. Ed. 39 (2000) 3168
4. Mannich C., and Kroesche W. Arch. Pharm. Ber. Dtsch. Pharm. Ges. (1912) 647
5. Kleinman E.F. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 2 (1991), Pergamon, Oxford 893
6. Ishimaru K., and Kojima T. Tetrahedron Lett. 44 (2003) 5441
7. Arend M., Westermann B., and Rish N. Angew. Chem. Int. Ed. 37 (1998) 1044
8. Arend M., Wetermannn R., and Risch N. Angew. Chem. Int. Ed. 31 (1992) 313
9. Tramontini M., and Angiolini L. Mannich Bases, Chemistry and Uses (1994), CRC, Boca Raton, FL
10. Sitzung D., and Meisenheimer H.J. Chem. Ber. (1907) 2096
11. Richey B.H.G., Mclane R.C., and Phillips C.J. Tetrahedron Lett. 17 (1976) 233
12. Itsuno S., Miyazaki K., and Ito K. Tetrahedron Lett. 27 (1986) 3033
13. Volkmann D.R.A., and Week D.D. Tetrahedron Lett. 27 (1986) 1549
14. Basha E.A., and Brook D.W. J. Chem. Soc. Chem. Commun. (1987) 305
15. Takenska H., Igoda M., and Endo T. J. Chem. Soc. Perkin Trans. 1 (1994) 413
16. Moody C.J., Lightfoot A.P., and Gallagher P.T. Synletter (1997) 659
17. Marco J.A., Carda M., Murga J., Gonzalez F., and Falomir E. Tetrahedron Lett. 38 (1997) 1841
18. Bottaro J.C., Bedford C.D., and Dodge A. Synth. Commun. (1985) 1333
19. We use O-trimethylsilyl hydroxylamine versus normal hydroxylamine salts because of good solubility of it in various organic solvent and fast syntheses of oxime ethers without needing to catalyst or pH control.
20. If we carried out the reaction without TMSCl, formation of desired product was not being observed.
21. We decide to complete these experiments by using allylsilane as a nucleophile. But, unfortunately we don't access to this compound for doing this.