Synthesis of 2-oxazolidinones by salen-Co-complexes catalyzed oxidative carbonylation of β-amino alcohols

Tetrahedron Letters

Volumn 48, Issue 6, 2007, Pages 929-932

  Liu, Jian Ming ^a,b   Peng, Xin Gao ^a,b   Liu, Jian Hua ^a,b   Zheng, Shu Zhan ^a,b   Sun, Wei ^a,b   Xia, Chun Gu ^a,b  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; AMINOALCOHOL; BETA AMINOALCOHOL; COBALT COMPLEX; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CARBONYLATION; CATALYST;

EID: 33846039971     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.028     Document Type: Article

References (40)

1. Gregory W.A., Brittelli D.R., Wang C.-L.J., Wuonola M.A., McRipley R.J., Eustice D.C., Eberly V.S., Bartholomew P.T., Slee A.M., and Forbes M. J. Med. Chem. 32 (1989) 1673
2. Seneci P., Caspani M., Ripamonti F., and Ciabatti R. J. Chem. Soc., Perkin Trans. 1 (1994) 2345
3. Grega K.C., Barbachyn M.R., Brickner S.J., and Mizsak S.A. J. Org. Chem. 60 (1995) 5255
4. Brickner S.J., Hutchinson D.K., Barbachyn M.R., Manninen R.R., Ulanowicz D.A., Garmon S.A., Grega K.C., Hendges S.K., Toops D.S., Ford C.W., and Zurenko G.E. J. Med. Chem. 39 (1996) 673
5. Lohray B.B., Baskaran S., Rao B.S., Reddy B.Y., and Rao I.N. Tetrahedron Lett. 40 (1999) 4855
6. Ager D.J., Prakash I., and Schaad D.R. Aldrichim. Acta 30 (1997) 3
7. Seydenpenne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis (1995), Wiley, NewYork
8. Ager D.J., Prakash I., and Schaad D.R. Chem. Rev. 96 (1996) 835
9. Köll P., and Lützen A. Tetrahedron: Asymmetry 7 (1996) 637
10. Lützen A., and Köll P. Tetrahedron: Asymmetry 8 (1997) 29
11. Lützen A., and Köll P. Tetrahedron: Asymmetry 8 (1997) 1193
12. Fonquerna S., Moyano A., Pericàs M.A., and Riera A. Tetrahedron: Asymmetry 8 (1997) 1685
13. Bravo P., Fustero S., Guidetti M., Volonterio A., and Zanda M. J. Org. Chem. 64 (1999) 8731
14. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis (2000), Wiley, New York
15. Bach J., Bull S.D., Davies S.G., Nicholson R.L., Sanganee H.J., and Smith A.D. Tetrahedron Lett. 40 (1999) 6677
16. O'Hagan D., and Tavasli M. Tetrahedron: Asymmetry 10 (1999) 1189
17. Yang L., Xu L.W., and Xia C.G. Tetrahedron Lett. 46 (2005) 3279
18. Puschin N.A., and Mitic R.V. Justus Leibigs Ann. Chem. 532 (1937) 300
19. Ono Y. Catal. Today 35 (1997) 15
20. Pachenco M.A., and Marshall C.L. Energy Fuels 11 (1997) 2
21. Delledonne D., Rivetti F., and Romano U. Appl. Catal. A: Gen. 221 (2001) 241
22. Wilson T. J. Org. Chem. 51 (1986) 2977
23. Imada Y., Mitsue Y., Ike K., Washizuka K., and Murahashi S. Bull. Chem. Soc. Jpn. 69 (1996) 2079
24. Li F.W., and Xia C.G. J. Catal. 227 (2004) 542
25. Chiarotto I., and Feroci M. Tetrahedron Lett. 42 (2001) 3451
26. Gabriele B., Salerno G., Brindisi D., Costa M., and Chiusoli G.P. Org. Lett. 2 (2000) 625
27. Gabriele B., Mancuso R., Salerno G., and Costa M. J. Org. Chem. 68 (2003) 601
28. Miller A.W., and Nguyen S.T. Org. Lett. 6 (2004) 2301
29. Tingoli M., Testaferri L., Temperini A., and Tiecco M.J. J. Org. Chem. 61 (1996) 6085
30. Bacchi A., Chiusoli G.P., Costa M., Gabriele B., Righi C., and Salerno G. Chem. Commun. (1997) 1209
31. Inesi A., Mucciante V., and Rossi L. J. Org. Chem. 63 (1998) 1337
32. Le Gendre P., Thominot P., Brunear C., and Dixneuf P.H. J. Org. Chem. 63 (1998) 1806
33. Takacs J.M., Jaber M.R., and Vellekoop A.S. J. Org. Chem. 63 (1998) 2742
34. Tenholte P., Thijs L., and Zwanenburg B. Tetrahedron Lett. 39 (1998) 7407
35. Sugiyama S., Watanabe S., and Ishii K. Tetrahedron Lett. 40 (1999) 7489
36. Vani P.S.N., Chida A.S., Srinivasan R., Chandrasekharam M., and Singh A.K. Synth. Commun. 31 (2001) 2043
37. 2 99.99% 0.2-0.3 MPa). The autoclave was placed in an oil bath pre-heated at 120 °C, and the whole reaction mixture was stirred for 2 h. After the reaction, the autoclave was cooled, and excess gas was purged slowly. The products were easily purified by column chromatography on silica gel.
38. Bolzacchini E., Meinardi S., Orlandi M., and Rindone B. J. Mol. Catal. A: Chem. 111 (1996) 281
39. Fukuda T., and Katsuki T. Tetrahedron 53 (1997) 7201
40. Belokon Y.N., Fuentes J., North M., and Steed J.W. Tetrahedron 60 (2004) 3191