β-Cyclodextrin promoted aza-Michael addition of amines to conjugated alkenes in water

Tetrahedron Letters

Volumn 47, Issue 13, 2006, Pages 2125-2127

  Surendra, K ^a   Krishnaveni, N Srilakshmi ^a   Sridhar, R ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Amino carbonyl compounds; Cyclodextrin; Amines; Aza Michael addition; Conjugated alkenes; Water

Indexed keywords

ALKENE DERIVATIVE; AMINE; BETA CYCLODEXTRIN; WATER;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CONJUGATION; REACTION ANALYSIS;

EID: 33344474544     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.124     Document Type: Article

References (60)

1. G. Bartoli, C. Cimarelli, E. Marcantoni, G. Palmieri, and M. Petrini J. Org. Chem. 59 1994 5328 5335
2. Y. Hayashi, J.J. Rode, and E.J. Corey J. Am. Chem. Soc. 118 1996 5502 5503
3. E.L. Eliel, and X.C. He J. Org. Chem. 55 1990 2114 2119
4. Y.F. Wang, T. Izawa, and S. Kobayashi J. Am. Chem. Soc. 104 1982 6465 6466
5. S. Hashiguchi, A. Kawada, and H. Natsugari J. Chem. Soc., Perkin Trans. 1 1991 2435 2444
6. G. Cardillo, and C. Tomasini Chem. Soc. Rev. 1996 117 128
7. E. Juaristi Enantioselective Synthesis of β-Amino Acids 1997 Wiley-VCH New York
8. G.I. George The Organic Chemistry of β-Lactams 1993 Wiley-VCH New York
9. P. Traxler, U. Trinks, E. Buchduger, H. Mett, T. Meyer, M. Muller, U. Regenass, J. Rosel, and N. Lydon J. Med. Chem. 38 1995 2441 2448
10. E. Juaristi, and H. Lopez-Ruiz Curr. Med. Chem. 6 1999 983 1004
11. D. Seebach, and J.L. Matthews Chem. Commun. 1997 2015 2016
12. W.J. Drury, D. Ferraris, C. Cox, B. Yong, and T. Leckta J. Am. Chem. Soc. 120 1998 11006 11007
13. E. Hagiwara, A. Fujii, and M. Sodeoka J. Am. Chem. Soc. 120 1998 2474 2475
14. A. Graul, and J. Castaner Drugs Future 22 1997 956 968
15. E.J. Corey, and G.A. Reichard Tetrahedron Lett. 30 1989 5207 5210
16. Y.J. Zou, H. Lei, X. Liu, and M. Zhang Org. Prep. Proced. Int. 23 1991 673 675
17. J. Frackenpohl, P.I. Arvidsson, J.V. Schreiber, and D. Seebach ChemBioChem 2 2001 445 455
18. M.E. Jung B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford 30
19. S. Kobayashi, and H. Ishitani Chem. Rev. 99 1999 1069 1094
20. H. Ishitani, M. Ueno, and S. Kobayashi J. Am. Chem. Soc. 122 2000 8180 8186
21. M. Arend, B. Westermann, and N. Risch Angew. Chem., Int. Ed. 37 1998 1044 1070
22. P. Perlmutter Conjugate Addition Reactions in Organic Synthesis 1992 Pergamon New York p 114
23. M. Perez, and R. Pleixates Tetrahedron 51 1995 8355 8362
24. N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y.S. Gyoung, and Y. Yamamoto J. Org. Chem. 62 1997 6274 6282
25. L. Fadini, and A. Togni Chem. Commun. 2003 30 31
26. S.D. Bull, S.G. Davies, S. Ballester, G. Fenton, P.M. Kelly, and A.D. Smith Synlett 2000 1257 1260
27. T.P. Loh, and L.L. Wie Synlett 1998 975 976
28. G. Bartoli, M. Bosco, E. Marcantoni, M. Petrini, L. Sambri, and E. Torregiani J. Org. Chem. 66 2001 9052 9055
29. S. Matsubara, M. Yashioka, and K. Utimoto Chem. Lett. 1994 827 828
30. T.C. Wabnitz, and J.B. Spencer Tetrahedron Lett. 43 2002 3891 3894
31. L.-W. Xu, and C.-G. Xia Tetrahedron Lett. 45 2004 4507
32. G. Jenner Tetrahedron Lett. 36 1995 233 236
33. N. Srivastava, and B.K. Banik J. Org. Chem. 68 2003 2109 2114
34. R. Varala, M.M. Alam, and S.R. Adapa Synlett 2003 720 722
35. N. Azizi, and M.R. Saidi Tetrahedron 60 2004 383 387
36. L. Yang, L.-W. Xu, and C.-G. Xia Tetrahedron Lett. 46 2005 3279 3282
37. J. Cabral, P. Laszlo, and L. Mahe Tetrahedron Lett. 30 1989 3969 3972
38. N.S. Shaikh, V.H. Deshpande, and A.V. Bedekar Tetrahedron 57 2001 9045 9048
39. J.S. Yadav, B.V.S. Reddy, A.K. Basak, and A.V. Narsaiah Chem. Lett. 32 2003 988 989
40. M.L. Kantam, V. Neeraja, B. Kavita, B. Neelima, M.K. Chaudhuri, and S. Hussain Adv. Synth. Catal. 347 2005 763 766
41. L.-W. Xu, J.-W. Li, S.-L. Zhou, and C.-G. Xia New. J. Chem. 28 2004 183 184
42. M.K. Chaudhuri, S. Hussain, M.L. Kantam, and B. Neelima Tetrahedron Lett. 46 2005 8329 8331
43. L.-W. Xu, J.-W. Li, C.-G. Xia, S.-L. Zhou, and X.-X. Hu Synlett 2003 2425 2427
44. B.C. Ranu, S.S. Dey, and A. Hajra Arkivoc 7 2002 76 81
45. B. Basu, P. Das, and I. Hossain Synlett 2004 2630 2632
46. P.T. Anastas, and J.C. Warner Green Chemistry, Theory and Practice 1998 Oxford University Press Oxford
47. P.T. Anastas T.C. Williamson Green Chemistry, Frontiers in Benign Chemical Synthesis and Processes 1998 Oxford University Press Oxford
48. Handbook of Green Chemistry and Technology; Clark, J.; Macquarrie, D.; Blackwell, M. A., Ed.; 2002.
49. M. Eissen, J.O. Metzger, E. Schmidt, and U. Schneidewind Angew. Chem., Int. Ed. 41 2002 414 436
50. P.A. Grieco Organic Synthesis in Water 1998 Blackie Academic and Professional London
51. C.-J. Li, and T.-H. Chan Organic Reactions in Aqueous Media 1997 John Wiley and Sons New York
52. H.C. Liang, S.K. Das, J.R. Galvan, S.M. Sato, Y. Zhang, L.N. Zakhrov, and A.L. Rheingold Green Chem. 7 2005 410 412
53. A. Lubineau, and J. Auge Tetrahedron Lett. 33 1992 8073 8074
54. N.S. Krishnaveni, K. Surendra, and K.R. Rao Chem. Commun. 2005 669 671
55. K. Surendra, N.S. Krishnaveni, V.P. Kumar, R. Sridhar, and K.R. Rao Tetrahedron Lett. 46 2005 4581 4583
56. K. Surendra, N.S. Krishnaveni, and K.R. Rao Synlett 2005 506 510
57. N.S. Krishnaveni, K. Surendra, and K.R. Rao Adv. Synth. Catal. 346 2004 346 350
58. K. Surendra, N.S. Krishnaveni, M.A. Reddy, Y.V.D. Nageswar, and K.R. Rao J. Org. Chem. 68 2003 9119 9121
59. K. Uekama, F. Hirayama, and T. Irie Chem. Rev. 98 1998 2045 2076
60. J. Szejtli J. Szejtli T. Osa Comprehensive Supramolecular Chemistry Vol. 3 1991 Pergamon Oxford 5 40