N,N,N′,N′-Tetramethyl-1,3-propanediamine as the catalyst of choice for the Baylis-Hillman reaction of cycloalkenone: Rate acceleration by stabilizing the zwitterionic intermediate via the ion-dipole interaction

Tetrahedron Letters

Volumn 45, Issue 28, 2004, Pages 5485-5488

  Young Lee, Ka ^a   Gowrisankar, Saravanan ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

Baylis Hillman reaction; Cycloalkenone; Ion dipole interaction; N,N,N ,N Tetramethyl 1,3 propanediamine; Zwitterion

Indexed keywords

1,3 PROPANEDIAMINE; AMPHOLYTE; CYCLOALKENE; CYCLOALKENONE; N,N,N',N' TETRAMETHYL 1,3 PROPANEDIAMINE; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CATALYST; DIPOLE; MOLECULAR INTERACTION;

EID: 2942684855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.064     Document Type: Article

References (57)

1. Basavaiah D., Rao A.J., Satyanarayana T. Chem. Rev. 103:2003;811
2. Kim J.N., Lee K.Y. Curr. Org. Chem. 6:2002;627
3. Basavaiah D., Rao P.D., Hyma R.S. Tetrahedron. 52:1996;8001
4. Ciganek E. Organic Reactions. Vol. 51:1997;201-350 John Wiley & Sons, New York
5. Drewes S.E., Roos G.H.P. Tetrahedron. 44:1988;4653
6. Langer P. Angew. Chem., Int. Ed. 39:2000;3049
7. Lesch B., Brase S. Angew. Chem., Int. Ed. 43:2004;115
8. Alcaide B., Almendrous P., Aragoncillo C., Rodriguez-Acebes R. J. Org. Chem. 69:2004;826
9. Trost B.M., Thiel O.R., Tsui H.-C. J. Am. Chem. Soc. 125:2003;13155
10. Evans C.A., Miller S.J. J. Am. Chem. Soc. 125:2003;12394
11. McDougal N.T., Schaus S.E. J. Am. Chem. Soc. 125:2003;12094
12. Lee K.Y., Kim J.M., Kim J.N. Tetrahedron. 59:2003;385
13. Lee K.Y., Kim J.M., Kim J.N. Synlett. 2003;357
14. Im Y.J., Lee C.G., Kim H.R., Kim J.N. Tetrahedron Lett. 44:2003;2987
15. Kim J.N., Kim J.M., Lee K.Y. Synlett. 2003;821
16. Kim J.N., Lee H.J., Lee K.Y., Kim H.S. Tetrahedron Lett. 42:2001;3737
17. Lee K.Y., Kim J.M., Kim J.N. Tetrahedron Lett. 44:2003;6737
18. Kim J.N., Lee K.Y., Kim H.S., Kim T.Y. Org. Lett. 2:2000;343
19. Xu Y.-M., Shi M. J. Org. Chem. 69:2004;417
20. Krishna P.R., Manjuvani A., Kannan V., Sharma G.V.M. Tetrahedron Lett. 45:2004;1183
21. Maher D.J., Connon S.J. Tetrahedron Lett. 45:2004;1301
22. Kim E.J., Ko S.Y., Song C.E. Helv. Chim. Acta. 86:2003;894
23. Shi M., Xu Y.-M., Zhao G.-L., Wu X.-F. Eur. J. Org. Chem. 2002;3666
24. Aggarwal V.K., Mereu A., Tarver G.J., McCague R. J. Org. Chem. 63:1998;7183
25. Yu C., Liu B., Hu L. J. Org. Chem. 66:2001;5413
26. Cai J., Zhou Z., Zhao G., Tang C. Org. Lett. 4:2002;4723
27. Aggarwal V.K., Dean D.K., Mereu A., Williams R. J. Org. Chem. 67:2002;510
28. Aggarwal V.K., Emme I., Fulford S.Y. J. Org. Chem. 68:2003;692
29. Kundu M.K., Mukherjee S.B., Balu N., Padmakumar R., Bhat S.V. Synlett. 1994;444
30. You J., Xu J., Verkade J.G. Angew. Chem., Int. Ed. 42:2003;5054
31. Gatri R., El Gaied M.M. Tetrahedron Lett. 43:2002;7835
32. Luo S., Wang P.G., Cheng J.-P. J. Org. Chem. 69:2004;555. and further references on the reaction rate cited therein
33. Iwama T., Kinoshita H., Kataoka T. Tetrahedron Lett. 40:1999;3741
34. Kataoka T., Iwama T., Tsujiyama S.-I. Chem. Commun. 1998;197
35. Kataoka T., Iwama T., Tsujiyama S.-I., Iwamura T., Watanabe S.-I. Tetrahedron. 54:1998;11813
36. Bauer T., Tarasiuk J. Tetrahedron: Asymmetry. 12:2001;1741
37. Kawamura M., Kobayashi S. Tetrahedron Lett. 40:1999;1539
38. Zhu Y.-H., Vogel P. Synlett. 2001;79
39. Pei W., Wei H.-X., Li G. Chem. Commun. 2002;2412
40. Rezgui F., El Gaied M.M. Tetrahedron Lett. 39:1998;5965
41. Sugahara T., Ogasawara K. Synlett. 1999;419
42. Yamada Y.M.A., Ikegami S. Tetrahedron Lett. 41:2000;2165
43. Shi M., Xu Y.-M. Chem. Commun. 2001;1876
44. Aggarwal V.K., Mereu A. Chem. Commun. 1999;2311
45. Li G., Wei H.-X., Gao J.J., Caputo T.D. Tetrahedron Lett. 41:2000;1
46. Patra A., Batra S., Joshi B.S., Roy R., Kundu B., Bhaduri A.P. J. Org. Chem. 67:2002;5783
47. Jauch J. J. Org. Chem. 66:2001;609
48. Lee K.Y., Gong J.H., Kim J.N. Bull. Korean Chem. Soc. 23:2002;659
49. Verkade J.G. Acc. Chem. Res. 26:1993;483
50. Hayase T., Shibata T., Soai K., Wakatsuki Y. Chem. Commun. 1998;1271
51. Collman J.P., Zhong M., Zhang C., Costanzo S. J. Org. Chem. 66:2001;7892
52. Sundermeier M., Zapf A., Mutyala S., Baumann W., Sans J., Weiss S., Beller M. Chem. Eur. J. 9:2003;1828
53. Rutherford J.L., Hoffmann D., Collum D.B. J. Am. Chem. Soc. 124:2002;264
54. Hoffmann D., Collum D.B. J. Am. Chem. Soc. 120:1998;5810
55. Basavaiah D., Krishnamacharyulu M., Jaganmohan Rao A. Synth. Commun. 30:2000;2061
56. 3: C, 71.54; H, 6.47. Found: C, 71.48; H, 6.51
57. 7