Facile Synthesis of α-Amino Nitrites Using Lanthanide Triflate as a Lewis Acid Catalyst

Synlett

Volumn 1997, Issue 1, 1997, Pages 115-116

  Kobayashi, Shu ^a   Ishitani, Haruro ^a   Ueno, Masaharu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002794514     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-719     Document Type: Article

References (28)

1. Shafran, Y. M.; Bakulev, V. A.; Mokrushin, V. S. Russian Chem. Rev. 1989, 55, 148.
2. (a) Weinstock, L. M.; Davis, P.; Handelsman, B.; Tull, R. J. Org. Chem. 1967, 32, 2823.
3. (b) Matier, W. L.; Owens, D. A.; Comer, W. T.; Deitchman, D.; Ferguson, H. C.; Seidehamel, R. J.; Young, J. R. J. Med. Chem. 1973, 16, 901.
4. Mai, K.; Patil, G. Tetrahedron Lett. 1984, 25, 4583.
5. Ojima, I.; Inaba, S.; Nakatsugawa, K. Chem. Lett. 1975, 331.
6. (a) Kobayashi, S. Synlett 1994, 689.
7. (b) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
8. (c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
9. (d) Kobayashi, S.; Ishitani, H. J. Chem. Soc., Chem. Commun. 1995, 1379.
10. (e) Kobayashi, S.; Moriwaki, M.; Hachiya, I. J. Chem. Soc., Chem. Commun. 1995, 1527.
11. (f) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1195.
12. (g) Kobayashi, S.; Moriwaki, M.; Hachiya, I. Synlett 1995, 1153.
13. (h) Kawada, A.; Mitamura, S.; Kobayashi, S. J. Chem. Soc., Chem. Commun. 1996, 183.
14. (i) Ishitani, H.; Nagayama, S.; Kobayashi, S. J. Org. Chem. 1996, 61, 1902.
15. (j) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.
16. (k) Kobayashi, S.; Hachiya, I.; Suzuki, S.; Moriwaki, M. Tetrahedron Lett. 1996, 37, 2809.
17. (l) Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, D. C.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731.
18. (m) Kobayashi, S.; Hachiya, I.; Yasuda, M. Tetrahedron Lett. 1996, 37, 5569.
19. (n) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977.
20. Cf. Kobayashi, S.; Araki, M.; Yasuda, M. Tetrahedron Lett. 1995, 56, 5773.
21. (a) Leblanc, J.; Gibson, H. W. Tetrahedron Lett. 1992, 33, 6295.
22. See also, (b) Chakraborty, T. K.; Reddy, G. V.; Hussain, K. A. Tetrahedron Lett. 1991, 32, 7597.
23. 3-catalyzed three-component reactions of aldehydes, amines, and imines proceeded smoothly to afford the corresponding α-amino nitriles in high yields. Cf. Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull Chem. Soc. Jpn. 1994, 67, 2342.
24. 3 instead of water is recommended.
25. (a) Kunz, H.; Sager, W. Angew. Chem., Int. Ed. Engl. 1987, 26, 557.
26. (b) Kunz, H.; Sager, W.; Pfengle, W.; Schanzenbach, D. Tetrahedron Lett. 1988, 29, 4397.
27. Cf. (c) Bellucci, C.; Cozzi, P. G.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7289.
28. Ishitani, H.; Kobayashi, S. Tetrahedron Lett. 1996, 37, 7357.