A Highly Efficient Catalyst FeCl3 in the Synthesis of α-Amino Phosphonates via Three-component Reactions
Jie Wu
Department of Chemistry, Fudan University, Shanghai 200433, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Tel.: 0086-21-5566-4619; Fax: 0086-21-6510-2412
Search for more papers by this authorWei Sun
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorWei-Zi Wang
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorHong-Guang Xia
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorJie Wu
Department of Chemistry, Fudan University, Shanghai 200433, China
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Tel.: 0086-21-5566-4619; Fax: 0086-21-6510-2412
Search for more papers by this authorWei Sun
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorWei-Zi Wang
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorHong-Guang Xia
Department of Chemistry, Fudan University, Shanghai 200433, China
Search for more papers by this authorAbstract
Three-component reactions of aldehydes, amines, and diethyl phosphite catalyzed by FeCl3 in EtOH or under solvent-free and mild conditions afforded the corresponding α-amino phosphonates in excellent yields.
REFERENCES
- 1For reviews of the biological activity of, α-amino phosphonic acids, see:
- 1a Hiratake, J.; Oda, J.. Biosci. Biotechnol. Biochem., 1997, 61, 211.
- 1b Kafarski, P.; Lejczak, B.. Phosphorus, Sulfur Silicon Relat. Elem., 1991, 63, 193 For a fM inhibitor of carboxypeptidase A, see:.
- 1c Kaplan, A. P.; Bartlett, P. A.. Biochemistry, 1991, 30, 8165.
- 2a Allen, J. G.; Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S. W.; Lambert, R. W.; Nisbet, L. J.; Ringrose, P. S.. Nature, 1978, 272, 56.
- 2b Pratt, R. F.. Science, 1989, 246, 917.
- 3 Maier, L.; Diel, P. J.. Phosphorus, Sulfur Silicon Relat. Elem., 1991, 57, 57.
- 4 Beers, S. A.; Schwender, C. F.; Loughney, D. A.; Malloy, E.; Demarest, K.; Jordan, J.. Bioorg. Med. Chem., 1996, 4, 1693.
- 5a Laschat, S.; Kunz, H.. Synthesis, 1992, 90.
- 5b Yadav, J. S.; Reddy, B. V. S.; Raj, K. S.; Reddy, K. B.; Prasad, A. R.. Synthesis, 2001, 2277.
- 6a Heydari, A.; Javidan, A.; Shaffie, M.. Tetrahedron Lett., 2001, 42, 8071.
- 6b Saidi, M. R.; Azizi, N.. Synlett, 2002, 1347.
- 6c Ranu, B. C.; Hajra, A.; Jana, U.. Org. Lett., 1999, 1, 1141.
- 6d Qian, C.; Huang, T.. J. Org. Chem., 1998, 63, 4125.
- 6e Manabe, K.; Kobayashi, S.. Chem. Commun., 2000, 669.
- 6f Lee, S.; Park, J. H.; Kang, J.; Lee, J. K.. Chem. Commun., 2001, 1698.
- 6g Chandrasekhar, S.; Prakash, S. J.; Jagadeshwar, V.; Narsihmulu, C.. Tetrahedron Lett., 2001, 42, 5561.
- 6h Yadav, J. S.; Reddy, B. V. S.; Madan, C.. Synlett, 2001, 1131.
- 6i Kaboudin, B.; Nazari, R.. Tetrahedron Lett., 2001, 42, 8211.
- 6j Zhan, Z.-P.; Li, J.-P.. Synth. Commun., 2005, 35, 2501.
- 6k Zhan, Z.-P.; Yang, R.-F.; Li, J.-P.. Chem. Lett., 2005, 34, 1042.
- 6l Reddy, K. R.; Reddy, K. S.; Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Reddy, V. V. N.. Chem. Lett., 2005, 34, 444.
- 6m Sun, P.; Hu, Z.; Huang, Z.. Synth. Commun., 2004, 34, 4293.
- 6n Ghosh, R.; Maiti, S.; Chakraborty, A.; Maiti, D. K.. J. Molecular Cat. A: Chemical, 2004, 210, 53.
- 6o Xu, F.; Luo, Y.; Deng, M.; Shen, Q.. Eur. J. Org. Chem., 2003, 4728.
- 6p Azizi, N.; Rajabi, F.; Saidi, M. R.. Tetrahedron Lett., 2004, 45, 9233.
- 7a Joly, G. D.; Jacobsen, E. N.. J. Am. Chem. Soc., 2004, 126, 4102.
- 7b Akiyama, T.; Sanada, M.; Fuchibe, K.. Synlett, 2003, 1463.
- 8a Bolm, C.; Legros, J.; Paih, J. L.; Zani, L.. Chem. Rev., 2004, 104, 6217.
- 8b Iwanami, K.; Aoyagi, M.; Oriyama, T.. Tetrahedron Lett., 2005, 46, 7487 and references cited therein.
- 8c Wu, J.; Zhang, L.; Diao, T.-N.. Synlett, 2005, 2653.
- 9a Toda, F.. Acc. Chem. Res., 1995, 28, 480.
- 9b
Metzger, J. O..
Angew. Chem., Int. Ed.,
1998,
37,
2975.
10.1002/(SICI)1521-3773(19981116)37:21<2975::AID-ANIE2975>3.0.CO;2-A CAS PubMed Web of Science® Google Scholar
- 9c Tanaka, K.; Toda, F.. Chem. Rev., 2000, 100, 1025.