One-pot synthesis of α-substituted hydroxylamine derivatives from aldehydes using lithium perchlorate/diethyl ether as a catalyst

Synthesis

Volumn , Issue 13, 2003, Pages 1962-1964

  Heydari, Akbar ^a   Mehrdad, Morteza ^b   Tavakol, Hossein ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

^b SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Lithium perchlorate; Oximes; substituted hydroxylamines

Indexed keywords

AMINES; CATALYSTS; DERIVATIVES; ETHERS; SUBSTITUTION REACTIONS;

REACTIVE SPECIES;

SYNTHESIS (CHEMICAL);

ALDEHYDE DERIVATIVE; ETHER; HYDROXYLAMINE; LITHIUM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SILYLATION;

EID: 0141618328     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41454     Document Type: Article

References (34)

1. (a) Bloch, R. Chem. Rev. 1998, 98, 1407.
2. (b) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
3. Risch, N.; Arend, N. In Stereoselective Synthesis (Houben-Weyl), Vol. 3; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme: Stuttgart, 1996, 1833-2009.
4. (a) Moody, C. J.; Lightfoot, A. P.; Gallagher, P. T. Synlett 1997, 659.
5. (b) Marco, J. A.; Carda, M.; Murga, J.; Gonzalez, F.; Falomir, E. Tetrahedron Lett. 1997, 38, 1841.
6. (c) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 5237.
7. (d) Dieter, R. K.; Datar, R. Can. J. Chem. 1993, 71, 814.
8. (e) Kolasa, T.; Sharma, S. K.; Miller, M. J. Tetrahedron 1998, 44, 5431.
9. (f) Yamamoto, Y.; Ito, W. Tetrahedron 1998, 44, 5415.
10. (g) Rodriques, K. E.; Basha, A.; Summers, J. B.; Brooks, D. W. Tetrahedron Lett. 1988, 29, 3455.
11. (h) Corey, E. J.; Nimura, K.; Konischi, Y.; Hashimoto, S.; Hamada, Y. Tetrahedron Lett. 1986, 27, 2199.
12. (i) Pirie, D. K.; Welch, W. M.; Weeks, P. D.; Volkmann, R. A. Tetrahedron Lett. 1986, 27, 1549.
13. (j) Ikeda, K.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1983, 24, 4707.
14. (k) Fiaud, J.-C.; Kagan, H. B. Tetrahedron Lett. 1971, 1019.
15. Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M. ; Fleming, I.; Schreiber, S. L., Eds.; Pergamon: Oxford, 1991, 355-396.
16. Itsuno, S.; Miyazaki, K.; Ito, K. Tetrahedron Lett. 1986, 27, 3033.
17. 2O has gained importance as a versatile reaction medium for effecting various organic transformations. For a review, see: Heydari, A. Tetrahedron 2002, 58, 6777.
18. (a) Hashimoto, M. US Patent, 4105156, 1976; Chem A bstr. 1980, 93, 150378.
19. (a) Hashimoto, M. US Patent, 4105156, 1976; Chem A bstr. 1980, 93, 150378.
20. (b) Kuroda, Y.; Okuhara, M.; Iguchi, E.; Aoki, H.; Imanaka, H.; Kamiya, T.; Hashimoto, H.; Hemmi, K.; Takeno, H. Ger.Offen. 2733658, 1978; Chem. Abstr. 1978, 89, 6413.
21. (b) Kuroda, Y.; Okuhara, M.; Iguchi, E.; Aoki, H.; Imanaka, H.; Kamiya, T.; Hashimoto, H.; Hemmi, K.; Takeno, H. Ger.Offen. 2733658, 1978; Chem. Abstr. 1978, 89, 6413.
22. (c) Kamiya, T.; Hemmi, K.; Takeno, H.; Hashimoto, M. Tetrahedron Lett. 1980, 21, 95.
23. (d) Hemmi, K.; Takeno, H.; Hashimoto, M.; Kamiya, T. Chem. Pharm. Bull. 1982, 30, 111.
24. Petrov, K. A.; Treshchalina, L. V.; Chizov, V. M. Zh. Obshch. Khim. 1979, 49, 590; Chem. Abstr. 1979, 91, 5305.
25. Petrov, K. A.; Treshchalina, L. V.; Chizov, V. M. Zh. Obshch. Khim. 1979, 49, 590; Chem. Abstr. 1979, 91, 5305.
26. Osipova, M. P.; Lukin, P. M.; Kukhtin, V. A. Zh. Obshch. Khim. 1982, 52, 449; Chem. Abstr. 1982, 96, 162861.
27. Osipova, M. P.; Lukin, P. M.; Kukhtin, V. A. Zh. Obshch. Khim. 1982, 52, 449; Chem. Abstr. 1982, 96, 162861.
28. Huber, R.; Knierzinger, A.; Obrecht, J. P.; Vasella, A. Helv. Chim. Acta 1985, 68, 1730.
29. Elhaddadi, M.; Petrus, J. R. C.; Petrus, F. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 57, 119.
30. Yuan, C.; Chen, S.; Zhou, H.; Maier, L. Synthesis 1993, 955.
31. 2O in the absence of LPDE at r.t. for 4 h, the corresponding O-(trimethylsilyl)oxime ether product was obtained in high yield.
32. (a) Evans, D. A.; Hurst, K. M.; Takacs, J. M. J. Am. Chem. Soc. 1978, 100, 3467.
33. (b) Okamoto, Y.; Azuhata, T.; Sakurai, H. Chem. Lett. 1981, 1265.
34. (c) Okamoto, Y.; Sakurai, H. Synthesis 1982, 497.