Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols

Tetrahedron

Volumn 59, Issue 13, 2003, Pages 2231-2239

  Salgado, Antonio ^a   Dejaegher, Yves ^a   Verniest, Guido ^a   Boeykens, Mark ^a   Gauthier, Christine ^a   Lopin, Christelle ^a   Tehrani, Kourosch Abbaspour ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Azetidin 3 ols; Azetidin 3 ones; Azetidines; Bromoimines

Indexed keywords

2 METHYLAZETIDIN 3 OL DERIVATIVE; 2 METHYLAZETIDIN 3 ONE DERIVATIVE; 3,3 DIMETHOXYAZETIDINE; AZETIDINE DERIVATIVE; BETA ALPHA,ALPHA DIMETHOXYKETIMINE; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CYCLIZATION; ISOMER; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037463814     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00241-2     Document Type: Article

References (27)

1. De Kimpe N. Padwa A., Katritzky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II, Three and Four-Membered Rings, with All Fused Systems Containing Four-Membered Rings. Vol. 1B:1996;Elsevier, Oxford. Chapter 1.18.
2. (a) De Kimpe N., Sulmon P., Schamp N. J. Chem. Soc., Chem. Commun. 1985;715-716
3. (b) De Kimpe N., Sulmon P., Schamp N. Tetrahedron. 44:1988;3653-3670
4. (c) De Kimpe N., Sulmon P., Schamp N. J. Org. Chem. 54:1989;2587-2590
5. (d) De Kimpe N., Sulmon P., Schamp N. Tetrahedron. 45:1989;2937-2955
6. (e) De Kimpe N., Stevens C. Synthesis. 1993;89-91
7. (f) De Kimpe N., De Smaele D. Tetrahedron Lett. 35:1994;8023-8026
8. (g) Aelterman W., De Kimpe N., Declercq J.-P. J. Org. Chem. 63:1998;6-11
9. (h) De Smaele D., Dejaegher Y., Duvey G., De Kimpe N. Tetrahedron Lett. 42:2001;2373-2375.
10. Salgado A., Boeykens M., Gauthier C., Declercq J.-P., De Kimpe N. Tetrahedron. 58:2002;2763-2775.
11. (a) Kobayashi J., Cheng J., Ishibashi M., Wälchli M.R., Yamamura S., Ohizumi Y. J. Chem. Soc., Perkin Trans. 1. 1991;1135-1137
12. (b) Takikawa H., Maeda T., Seki M., Koshino H., Mori K. J. Chem. Soc., Perkin Trans. 1. 1997;97-111
13. (c) Knapp S., Dong Y. Tetrahedron Lett. 38:1997;3813-3816.
14. For previous syntheses of azetidin-3-one derivatives, see: (a) Moyer M.P., Feldman P.L., Rapoport H. J. Org. Chem. 50:1985;5223-5230 (b) Podlech J., Seebach D. Helv. Chim. Acta. 78:1995;1238-1246 (c) Frigola J., Torrens A., Castillo J.A., Mas J., Vañó D., Berrocal J.M., Calvet C., Salgado L., Redondo J., García-Granda S., Valentí E., Quintana J.R. J. Med. Chem. 37:1994;4195-4210 (d) Dejaegher Y., Kuzmenok N.M., Zvonok A.M., De Kimpe N. Chem. Rev. 102:2002;29-60.
15. For previous syntheses of azetidin-3-one derivatives, see: (a) Moyer M.P., Feldman P.L., Rapoport H. J. Org. Chem. 50:1985;5223-5230 (b) Podlech J., Seebach D. Helv. Chim. Acta. 78:1995;1238-1246 (c) Frigola J., Torrens A., Castillo J.A., Mas J., Vañó D., Berrocal J.M., Calvet C., Salgado L., Redondo J., García-Granda S., Valentí E., Quintana J.R. J. Med. Chem. 37:1994;4195-4210 (d) Dejaegher Y., Kuzmenok N.M., Zvonok A.M., De Kimpe N. Chem. Rev. 102:2002;29-60.
16. For previous syntheses of azetidin-3-one derivatives, see: (a) Moyer M.P., Feldman P.L., Rapoport H. J. Org. Chem. 50:1985;5223-5230 (b) Podlech J., Seebach D. Helv. Chim. Acta. 78:1995;1238-1246 (c) Frigola J., Torrens A., Castillo J.A., Mas J., Vañó D., Berrocal J.M., Calvet C., Salgado L., Redondo J., García-Granda S., Valentí E., Quintana J.R. J. Med. Chem. 37:1994;4195-4210 (d) Dejaegher Y., Kuzmenok N.M., Zvonok A.M., De Kimpe N. Chem. Rev. 102:2002;29-60.
17. For previous syntheses of azetidin-3-one derivatives, see: (a) Moyer M.P., Feldman P.L., Rapoport H. J. Org. Chem. 50:1985;5223-5230 (b) Podlech J., Seebach D. Helv. Chim. Acta. 78:1995;1238-1246 (c) Frigola J., Torrens A., Castillo J.A., Mas J., Vañó D., Berrocal J.M., Calvet C., Salgado L., Redondo J., García-Granda S., Valentí E., Quintana J.R. J. Med. Chem. 37:1994;4195-4210 (d) Dejaegher Y., Kuzmenok N.M., Zvonok A.M., De Kimpe N. Chem. Rev. 102:2002;29-60.
18. Chan T.H., Brook M.A., Chaly T. Synthesis. 1983;203-205.
19. Jacobson R.M., Raths R.A., McDonald J.H. III. J. Org. Chem. 42:1977;2545-2549.
20. Feuerer A., Severin T. J. Org. Chem. 59:1994;6026-6029.
21. Grady G.L., Chokshi S.K. Synthesis. 1972;483-484.
22. De Kimpe N., Rocchetti M.T. J. Agric. Food Chem. 46:1998;2278-2281.
23. (a) Harada K. Patai S. The Chemistry of the Carbon-Nitrogen Double Bond. 1970;Wiley-Interscience, New York,
24. (b) Borch R.F., Durst H.D. J. Am. Chem. Soc. 91:1969;3996-3997.
25. Friebolin H. Ein- und Zweidimensionale NMR-Spektroskopie. 2nd ed. 1992;VCH, Weinheim. p 94.
26. For some methods of asymmetric imine reduction, see: (a) Inoue T., Sato D., Komura K., Itsuno S. Tetrahedron Lett. 40:1999;5379-5382 (b) Itsuno S., Matsumoto T., Sato D., Inoue T. J. Org. Chem. 65:2000;5879-5881.
27. For some methods of asymmetric imine reduction, see: (a) Inoue T., Sato D., Komura K., Itsuno S. Tetrahedron Lett. 40:1999;5379-5382 (b) Itsuno S., Matsumoto T., Sato D., Inoue T. J. Org. Chem. 65:2000;5879-5881.