Aldol condensations of aldehydes and ketones catalyzed by primary amine on water

Asian Journal of Chemistry

Volumn 24, Issue 2, 2012, Pages 751-755

  Zhang, Xu ^a   Xiong, Yan ^a   Zhang, Shuting ^a   Ling, Xuege ^a   Wang, Jinyue ^b   Chen, Changguo ^a  

^a CHONGQING UNIVERSITY   (China)

^b YIBIN UNIVERSITY   (China)

Author keywords

Aldol condensations; Glycine; Heterogeneous catalysis; Primary amine; , Unsaturated ketones

Indexed keywords

EID: 84861604564     PISSN: 09707077     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, Ch. 2 and 3 (1992).
2. C.H. Heathcock, in eds. B.M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon, Oxford, Vol. 2, p. 133 (1991).
3. A. Yanagisawa, R. Goudu and T. Arai, Org. Lett., 6, 4281 (2004).
4. D.S. Noyce and L.R. Snyder, J. Am. Chem. Soc., 81, 620 (1959).
5. C.U. Pittman, Jr. and Y.F. Liang, J. Org. Chem., 45, 5048 (1980).
6. (a) A. Guida, M.H. Lhouty, D. Tichit, F. Figueras and P. Geneste, Appl. Catal. A: Gen., 164, 251 (1997)
7. (b) J.C.A.A. Roelofs, D.J. Lensveld, A.J. van Dillen and K.P. de Jong, J. Catal., 203, 184 (2001)
8. (c) J.C.A.A. Roelofs, A.J. van Dillen and K.P. de Jong, Catal. Lett., 74, 91 (2001)
9. (d) M.J. Climent, A. Corma, S. Iborra and A. Velty, J. Catal., 221, 474 (2004).
10. (a) D.S. Noyce and W.L. Reed, J. Am. Chem. Soc., 81, 624 (1959)
11. (b) S.A. Fine and P.D. Pulaski, J. Org. Chem., 38, 1747 (1973).
12. P.S. Gradeff, US Patent 3840601 (1974)
13. (b) J.V. Sinisterra, A. Garcia-Raso, J.A. Cabello and J.M. Marinas, Synthesis, 502 (1984).
14. N. Iranpoor and F. Kazemi, Tetrahedron, 54, 9475 (1998).
15. W.B. Yi and C. Cai, J. Fluorine Chem., 126, 1553 (2005).
16. A. Dhakshinamoorthy, M. Alvaro and H. Garcia, Adv. Synth. Catal., 352, 711 (2010).
17. K. Irie and K. Watanabe, Bull. Chem. Soc. (Japan), 53, 1366 (1980).
18. I. Cota, R. Chimentao, J. Sueiras and F. Medina, Catal. Commun., 9, 2090 (2008).
19. W. Wang, J. Wang, H. Li and L.X. Liao, Tetrahedron Lett., 45, 7235 (2004).
20. W. Wang, Y.J. Mei, H. Li and J. Wang, Org. Lett., 7, 601 (2005).
21. S.D. Yang, L.Y. Wu, Z.Y. Yan, Z.L. Pan and Y.M. Liang, J. Mol. Catal. A: Chem., 268, 107 (2007).
22. J.F. Wang, M. Lei, Q. Li, Z.M. Ge, X. Wang and R.T. Li, Tetrahedron, 65, 4826 ( 2009).
23. R.N. Butler and A.G. Coyne, Chem. Rev., 110, 6302 (2010).
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, Gaussian Inc., Gaussian03, Revision E.01, Pittsburgh PA (2003).
25. (a) Z. Tang, F. Jiang, L.T. Yu, X. Cui, L.Z. Gong, A.Q. Mi, Y.Z. Jiang and Y.D. Wu, J. Am. Chem. Soc., 125, 5262 (2003)
26. (b) Z. Tang, F. Jiang, X. Cui, L.Z. Gong, A.Q. Mi, Y.Z. Jiang and Y.D. Wu, Proc. Natl. Acad. Sci., 101, 5755 (2004)
27. (c) Z. Tang, Z.H. Yang, X.H. Chen, L.F. Cun, A.Q. Mi, Y.Z. Jiang and L.Z. Gong, J. Am. Chem. Soc., 127, 9285 (2005)
28. (d) B. List, Chem. Commun., 8, 819 (2006)
29. (e) X.Y. Xu, Y.Z. Wang and L.Z. Gong, Org. Lett., 9, 4247 (2007)
30. (f) J. Liu, Z.G. Yang, Z. Wang, F. Wang, X.H. Chen, X.H. Liu, X.M. Feng, Z.S. Su and C.W. Hu, J. Am. Chem. Soc., 130, 5654 (2008)
31. (g) Y. Xiong, F. Wang, S.X. Dong, X.H. Liu and X.M. Feng, Synlett, 73 (2008).
32. (a) M.P. Lalonde, Y.G. Chen and E.N. Jacobsen, Angew. Chem., 118, 6514 (2006)
33. Angew. Chem. Int. Ed., 45, 6366 (2006)
34. (b) S.Z. Luo, H. Xu, J.Y. Li, L. Zhang and J.P. Cheng, J. Am. Chem. Soc., 129, 3074 (2007)
35. (c) Y. Xiong, Y.H. Wen, F. Wang, B. Gao, X.H. Liu, X. Huang and X.M. Feng, Adv. Synth. Catal., 349, 2156 (2007)
36. (d) S.Z. Luo, Y.P. Qiao, L. Zhang, J.Y. Li, X. Li and J.P. Cheng, J. Org. Chem., 74, 9521 (2009).