Synthesis of vinyloxazolidinones by palladium-catalyzed CO2-recycling reaction of 4-(benzylamino)-2-butenyl carbonates

Tetrahedron Letters

Volumn 48, Issue 49, 2007, Pages 8678-8682

  Yoshida, Masahiro ^a   Ohsawa, Yusuke ^b   Sugimoto, Kenji ^b   Tokuyama, Hidetoshi ^b   Ihara, Masataka ^c  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 (BENZYLAMINO) 2 BUTENYL CARBONATE DERIVATIVE; CARBON DIOXIDE; CARBONIC ACID; OXAZOLIDINONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; VINYLOXAZOLIDINONE DERIVATIVE;

ARTICLE; CARBON FIXATION; CATALYSIS; CHEMICAL STRUCTURE; ELIMINATION REACTION; SYNTHESIS;

EID: 35748957504     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.020     Document Type: Article

References (37)

1. Park C.-H., Brittelli D.R., Wang C.L.-J., Marsh F.D., Gregory W.A., Wuonola M.A., McRipley R.J., Eberly V.S., Slee A.M., and Forbes M. J. Med. Chem. 35 (1992) 1156
2. Brickner S.J., Hutchinson D.K., Barbachyn M.R., Manninen P.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
3. Lohray B.B., Baskaran S., Rao B.S., Reddy B.Y., and Rao I.N. Tetrahedron Lett. 40 (1999) 4855
4. Selvakumar N., Srinivas D., Khera M.K., Kumar M.S., Mamigi R.N.V.S., Sarnaik H., Charavaryamath C., Rao B.S., Raheem M.A., Das J., Iqbal J., and Rajagopalan R. J. Med. Chem. 45 (2002) 3953
5. Barbachyn M.R., and Ford C.W. Angew. Chem., Int. Ed. 42 (2003) 2010
6. Kawanami H., Matsumoto H., and Ikushima Y. Chem. Lett. 34 (2005) 60
7. Hancock M.T., and Pinhas A.R. Synthesis (2004) 2347
8. Shen Y.-M., Duan W.-L., and Shi M. Eur. J. Org. Chem. (2004) 3080
9. Miller A.W., and Nguyen S.T. Org. Lett. 6 (2004) 2301
10. Sudo A., Morioka Y., Sanda F., and Endo T. Tetrahedron Lett. 45 (2004) 1363
11. Sudo A., Morioka Y., Koizumi E., Sanda F., and Endo T. Tetrahedron Lett. 44 (2003) 7889
12. Kawanami H., and Ikushima Y. Tetrahedron Lett. 43 (2002) 3841
13. Tascedda P., and Dunach E. Chem. Commun. (2000) 449
14. Maggi R., Bertolotti C., Orlandini E., Oro C., Sartori G., and Selva M. Tetrahedron Lett. 48 (2007) 2131
15. Feroci M., Orsini M., Sotgiu G., Rossi L., and Inesi A. J. Org. Chem. 70 (2005) 7795
16. Shi M., and Shen Y.-M. J. Org. Chem. 67 (2002) 16
17. Bacchi A., Chiusoli G.P., Costa M., Gabriele B., Righi C., and Salerno G. Chem. Commun. (1997) 1209
18. Costa M., Chiusoli G.P., and Rizzardi M. Chem. Commun. (1996) 1699
19. Coppola G.M., and Damon R.E. J. Heterocyclic Chem. 32 (1995) 1133
20. Mitsudo T., Hori Y., Yamakawa Y., and Watanabe Y. Tetrahedron Lett. 28 (1987) 4417
21. 2:. Shi M., and Shen Y.-M. Curr. Org. Chem. 7 (2003) 737
22. 2 source. Feroci M., Inesi A., Mucciante V., Rossi L. Tetrahedron Lett. 40 (1999) 6059
23. Arcadi A., Inesi A., Marinelli F., Rossi L., and Verdecchia M. Synlett (2005) 67
24. Yoshida M., and Ihara M. Chem. Eur. J. (2004) 2886
25. Yoshida M., and Ihara M. Angew. Chem., Int. Ed. 40 (2001) 616
26. Yoshida M., Fujita M., Ishii T., and Ihara M. J. Am. Chem. Soc. 125 (2003) 4874
27. Yoshida M., Fujita M., and Ihara M. Org. Lett. 5 (2003) 3325
28. Yoshida M., Ohsawa Y., and Ihara M. J. Org. Chem. 69 (2004) 1590
29. Yoshida M., Ohsawa Y., and Ihara M. Tetrahedron 62 (2006) 11218
30. 2: C, 75.25; H, 7.80; N, 5.16. Found: C, 75.37; H, 7.84; N, 5.07.
31. +), found 227.1657.
32. Synthesis of vinylaziridines by the palladium-catalyzed reaction of allylic carbonates has been reported. Ohno H., Ishii K., Honda A., Tamamura H., Fujii N., Takemoto Y., and Ibuka T. J. Chem. Soc., Perkin Trans. 1 (1998) 3703
33. When the reaction of 1h, which has no substituents at the allylic position, was examined, the complex mixture was yielded. In this case, β-elimination of palladium from the intermediate π-allylpalladium complex would occur to cause the undesired reactions{A figure is presented}.
34. Pérez E.R., da Silva M.O., Costa V.C., Rodrigues-Filho U.P., and Franco D.W. Tetrahedron Lett. 43 (2002) 4091
35. Pérez E.R., Santos R.H.A., Gambardella M.T.P., de Macedo L.G.M., Rodrigues-Filho U.P., Launay J.-C., and Franco D.W. J. Org. Chem. 69 (2004) 8005
36. 3N, pyridine and DABCO were employed.
37. As another possibility for the role of DBU, it is presumed that DBU acts as a ligand for palladium catalyst. Takimoto M., and Mori M. J. Am. Chem. Soc. 123 (2001) 2895