Highly efficient phosphine-catalyzed aza-Michael reactions of α,β-unsaturated compounds with carbamates in the presence of TMSCl

Tetrahedron Letters

Volumn 45, Issue 23, 2004, Pages 4507-4510

  Xu, Li Wen ^a   Xia, Chun Gu ^a  

^a LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Aza Michael; Carbamates; Conjugate addition; Enones; Phosphine

Indexed keywords

CARBAMIC ACID DERIVATIVE; CHALCONE; PHOSPHINE; TRANSITION ELEMENT;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CONJUGATE; MICHAEL ADDITION; REACTION ANALYSIS;

EID: 2342543197     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.053     Document Type: Article

References (58)

1. Drury W.J., Ferraris D., Cox C., Young B., Leckta T. J. Am. Chem. Soc. 120:1998;11006
2. Hagiwara E., Fujii A., Sodeoka M. J. Am. Chem. Soc. 120:1998;2474
3. Abele S., Seebach D. Eur. J. Org. Chem. 6:2000;1
4. Varala R., Alam M.M., Adapa S. Synlett. 2003;720
5. Fringuelli F., Pizzo F., Rucci M., Vaccaro L. J. Org. Chem. 68:2003;7041
6. Duursma A., Minnaard A.J., Feringa B.L. J. Am. Chem. Soc. 125:2003;3700
7. Gnad F., Reiser O. Chem. Rev. 103:2003;1603
8. Jung M.E. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 4:1991;30 Pergamon, Oxford
9. Kobayashi S., Ishitani H. Chem. Rev. 99:1999;1069
10. Manabe K., Kobayashi S. Org. Lett. 1:1999;1965
11. Okitsu O., Oyamada H., Furuta T., Kobayashi S. Heterocycles. 52:2000;1143
12. Ishitani H., Ueno M., Kobayashi S. J. Am. Chem. Soc. 122:2000;8180
13. Arend M., Westermann B., Risch N. Angew. Chem., Int. Ed. 37:1998;1044
14. Kobayashi S., Kakumoto K., Sugiura M. Org. Lett. 4:2002;1319
15. Enders D., Muller S.F., Raabe G. Angew. Chem., Int. Ed. 38:1999;195
16. Gaunt M.J., Spencer J.B. Org. Lett. 3:2001;25
17. Enders D., Wallert S. Synlett. 2002;304
18. Wabnitz T.C., Spencer J.B. Tetrahedron Lett. 43:2002;3891
19. Xu L.W., Xia C.G., Hu X.X. Chem. Commun. 2003;2570
20. Xu L.W., Li J.W., Xia C.G., Zhou S.L., Hu X.X. Synlett. 2003;2425
21. Xu L.W., Li L., Xia C.G., Zhou S.L., Li J.W., Hu X.X. Synlett. 2003;2337
22. Xu L.W., Xia C.G., Li J.W., Zhou S.L. Synlett. 2003;2246
23. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. 1992;Pergamon, New York. p 114
24. Perez M., Pleixates R. Tetrahedron. 51:1995;8355
25. Asao N., Shimada T., Sudo T., Tsukada N., Yazawa K., Gyoung Y.S., Yamamoto Y. J. Org. Chem. 62:1997;6274. and references cited therein
26. Bull S.D., Davies S.G., Delgado-Ballester S., Fenton G., Kelly P.M., Smith A.D. Synlett. 2000;1257
27. Fadini L., Togni A. Chem. Commun. 2003;30
28. Sani M., Bruche L., Chiva G., Fustero S., Piera J., Volonterio A., Zanda M. Angew. Chem., Int. Ed. 42:2003;2060
29. Matsubara S., Yoshioka M., Utimoto K. Chem. Lett. 1994;827
30. Loh T.P., Wei L.L. Synlett. 1998;975
31. Kawatsura M., Hartiwig J.F. Organometallic. 20:2001;1960
32. Sibi M.P., Manyem S. Tetrahedron. 56:2000;8033
33. Zhuang W., Hazell R.G., Jørgensen K.A. Chem. Commun. 2001;1240
34. Sibi M.P., Liu M. Org. Lett. 2:2000;3393
35. Sibi M.P., Shay J.J., Liu M., Jasperse C.P. J. Am. Chem. Soc. 120:1998;6615
36. Bartoli G., Bosco M., Marcantoni E., Pertrini M., Sambri L., Torregiani E. J. Org. Chem. 66:2001;9052
37. Srivastava N., Banik B.K. J. Org. Chem. 68:2003;2109
38. Gaunt M.J., Spencer J.B. Org. Lett. 3:2001;25
39. Wabnitz T.C., Spencer J.B. Tetrahedron Lett. 43:2002;3891
40. Wabnitz T.C., Yu J.Q., Spencer J.B. Synlett. 2003;1070
41. Wabnitz T.C., Spencer J.B. Org. Lett. 5:2003;2141
42. Christmann M., Bhatt U., Quitschalle M., Claus E., Kalesse M. Angew. Chem., Int. Ed. 39:2000;4364
43. Mulzer J., Mantoulidis A., Öhler E. J. Org. Chem. 65:2000;7456
44. Gololobov Y.G., Kasukhin L.F. Tetrahedron. 48:1992;1353
45. Kato H., Ohmori K., Suzuki K. Synlett. 2001;1003
46. Anderson N.G., Lust D.A., Colapret K.A., Simpson J.H., Malley M.F., Gougoutas J.Z. J. Org. Chem. 61:1996;7955
47. Weissman S.A., Rossen K., Reider P. J. Org. Lett. 3:2001;2513
48. Hayashi T., Shibata T., Soai K., Wakasuki Y. Chem. Commun. 1998;1271
49. Jenner G. Tetrahedron Lett. 41:2000;3091
50. Shi M., Jiang J.K., Cui S.C., Feng Y.S. J. Chem. Soc. Perkin Trans. 1. 2001;390
51. Shi M., Chen L.H. Chem. Commun. 2003;1310
52. Trost B.M., Dake G.R. J. Am. Chem. Soc. 119:1997;7595-7596
53. Lu X., Zhang C., Xu Z. Acc. Chem. Res. 34:2001;535
54. Wróblewski A.E., Verkade J.G. J. Org. Chem. 67:2002;420
55. Fan R.H., Hou X.L. J. Org. Chem. 68:2003;726
56. Stewart I.C., Bergman R.G., Toste F.D. J. Am. Chem. Soc. 125:2003;8696
57. White D.A., Baizer M.M. Tetrahedron Lett. 14:1973;3597
58. 3Cl: C 65.16, H 5.43, N 4.22. Found: C 65.12, H 5.41, N 4.25