Direct aldol reactions catalyzed by 1,1,3,3-tetramethylguanidine lactate without solvent

Green Chemistry

Volumn 7, Issue 7, 2005, Pages 514-517

  Zhu, Anlian ^a   Jiang, Tao ^a   Wang, Dong ^a   Han, Buxing ^a   Liu, Li ^a   Huang, Jun ^a   Zhang, Jicheng ^a   Sun, Donghai ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 22544453004     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b501925g     Document Type: Article

References (33)

1. C. H. Heathcock, in Comprehensive Organic Synthesis, Vol. 2, ed. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991.
2. (a) S. D. Rychonvsky, Chem. Rev., 1995, 95, 2021;
3. (b) K. C. Nicklaw, D. Vourlounis, N. Winssinger and P. S. Baran, Angew. Chem., Int. Ed., 2000, 37, 44.
4. (a) T. K. Hollis and B. J. Bosnich, J. Am. Chem. Soc., 1995, 117, 4570;
5. (b) S. E. Denmark and W. J. Lee, Org. Chem., 1994, 59, 707;
6. (c) H. Li, H. Tian, Y. Chen, D. Wang and C. Li, Chem. Commun., 2002, 2994.
7. A. Yanagisawa, H. Takahashi and T. Arai, Chem. Commun., 2004, 580.
8. For reviews of direct catalytic aldol reactions: (a) B. Alcaide and P. Almendros, Eur. J. Org. Chem., 2002, 1595;
9. (b) B. List, Tetrahedron, 2002, 58, 5573;
10. (c) M. Shibasaki and N. Yashikawa, Chem. Rev., 2002, 102, 2187.
11. For aldol reactions catalyzed by amino acid, see: (a) B. List, R. A. Lerner and C. F. Barbas, III, J. Am. Chem. Soc., 2000, 122, 2395;
12. (b) S. Chandrasekhar, C. Narsihmulu, N. R. Reddy and S. S. Sultana, Chem. Commun., 2004, 2450;
13. (c) K. Sakthivel, W. Notz, T. Bui and C. F. Barbas, III, J. Am. Chem. Soc., 2001, 123, 5260;
14. (d) T. Loh, L. Feng, H. Yang and J. Yang, Tetrahedron Lett., 2002, 42, 8741.
15. For aldol reactions catalyzed by complex based on alkaline or alkaline earth metal, see: (a) Y. Wu, W. Shao, C. Zheng, Z. Huang, J. Cai and Q. Deng, Helv. Chim. Acta, 2004, 87, 1377;
16. (b) H. Wei, R. L. Jasoni, H. Shao, J. Hu and D. W. Paré, Tetrahedron, 2004, 60, 11829.
17. For aldol reaction promoted by Zn or Zn-proline, see: (a) N. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi and M. Shibasaki, J. Am. Chem. Soc., 2003, 125, 2169;
18. (b) T. Darbre and M. Machuqueiro, Chem. Commun., 2003, 1090.
19. (a) C. M. Gasparsk and M. J. Miller, Tetrahedron, 1991, 29, 5367;
20. (b) M. Horikawa, J. Busch-Petersen and E. J. Corey, Tetrahedron Lett., 1999, 40, 3843.
21. (a) R. Sercheli, A. L. B. Ferreira, M. C. Guerreiro, R. M. Vargas, R. A. Sheldon and U. Schuchardt, Tetrahedron Lett., 1997, 38, 1325;
22. (b) R. Sercheli, R. M. Vargas, R. A. Sheldon and U. Schuchardt, J. Mol. Catal A: Chem., 1999, 148, 173.
23. For reviews for the utilization of ionic liquid in organic synthesis, see: (a) T. Welton, Chem. Rev., 1999, 99, 2071;
24. (b) P. Wasserscherd and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772;
25. (c) R. Sheldon, Chem. Commun., 2001, 2399;
26. (d) J. Dupont, R. F. de Souza and P. A. Z. Auarez, Chem. Rev., 2002, 102, 3667.
27. (a) W. A. Herrenmann, Angew. Chem., Int. Ed., 2001, 41, 1290;
28. (b) C. P. Mehnert, N. C. Dispenziere and R. A. Cook, Chem. Commun., 2002, 1610.
29. (a) D. Zhao, Z. Fei, T. J. Geldbach, R. Scopelliti and P. J. Dyson, J. Am. Chem. Soc., 2004, 126, 15876;
30. (b) H. X. Gao, B. X. Han, J. C. Li, T. Jiang, Z. M. Liu, W. Z. Wu, Y. H. Chang and J. M. Zhang, Synth. Commun., 2004, 34, 17, 3083;
31. (c) N. M. M. Mateus, L. C. Branco, M. M. T. Lourenco and C. A. M. Afonso, Green Chem., 2003, 5, 347.
32. T. Jiang, H. Gao, B. Han, G. Zhao, Y. Chang, W. Wu, L. Gao and G. Yang, Tetrahedron Lett., 2004, 45, 2699.
33. J. Huang, T. Jiang, H. Gao, B. Han, Z. Liu, W. Wu, Y. Chang and G. Zhao, Angew. Chem., Int. Ed., 2004, 43, 1397.