Aziridine synthesis in protic media by using lanthanide triflates as catalysts

Tetrahedron

Volumn 55, Issue 45, 1999, Pages 12929-12938

  Xie, Wenhua ^a   Fang, Jianwen ^a   Li, Jun ^a   Wang, Peng George ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

Aziridines; Diazo compounds; Imines; Lanthanides

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE; AROMATIC AMINE; AZIRIDINE; DIAZOMETHANE; DIAZONIUM COMPOUND; IMINE; LANTHANIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033527809     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00791-7     Document Type: Article

References (40)

1. (a) Muller, P. in Advances in Catalytic Processes: Vol. 2 Asymmetric Catalysis; Doyle, M. P. Ed. JAI Press: Greenwich, CT, 1997.
2. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. Comprehensive Heterocyclic Chemistry II; Padwa, A. Ed.; Pergamon: USA, 1996, Vol. 1A, p1.
3. (c) Kump, J. E. G.; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p469.
4. (d) Tanner, D. Angew. Chem. Int. Ed. Engl. 1994, 33, 599.
5. (e) Tanner, D. Pure Appl. Chem. 1993, 65, 1319.
6. (f) Hudlicky, T.; Seoane, G.; Price, J. D.; Gadamasetti, K. G. Synlett 1990, 433.
7. (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
8. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Andersen, B. A.; Bames, D. M. J. Am. Chem. Soc. 1993, 115, 5328.
9. (c) Harm, A. M.; Knight, J. G.; Stemp, G. Tetrahedron Lett. 1996, 37, 6189.
10. (d) Li, Z.; Conser, K. R.; Jacobson, E. N. J. Am Chem. Soc. 1993, 115, 5326.
11. (e) Li, Z.; Quan, R. W.; Jacobson, E. N. J. Am Chem. Soc. 1995, 117, 5889.
12. (f) Müller, P.; Baud, C.; Jacueier, Y. Tetrahedron 1996, 52, 1543.
13. (a) Hansen, K. B.; Finney, N. S.; Jacobson, E. N. Angew Chem. Int. Ed. Engl. 1995, 34, 676.
14. (b) Rasmussen, K. G.; Jørgensen, K. A. J. Chem. Soc. Chem. Commun. 1995, 1401.
15. (c) Moran, M.; Bemardinelli, G.; Müller, P. Hev. Chem. Acta 1996, 78, 2048.
16. (d) Zhu, Z.; Espenson, J. H. J. Am. Chem. Soc. 1996, 118, 9901.
17. (e) Mohan, J. M.; Uphade, B. S.; Choudhary, V. R.; Ravindranathan, T.; Sdalai, A. Chem. Commun. 1997, 1429.
18. Casarrubios, L.; Pérez, J. A.; Brookhart, M.; Templeton, J. L. J. Org. Chem. 1996, 61, 8358.
19. Rasmussen, K. G.; Hazell, R. G.; Jørgensen, K. A.; Chem. Commun. 1997, 1103.
20. For reviews see: (a) Marshman, R. Aldrichimica Acta 1995, 28, 77.
21. (b) Kobayashi, S. Synlett 1994, 689.
22. (a) Kobayashi, S.; Nagayarna, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.
23. (b) Kobayashi, S.; Busujima, T.; Nagayatna, S. Chem. Commun. 1998, 19.
24. (c) Heaney, H.; Simcox, M. T.; Slawin, A. M. Z.; Giles, R. G. Synlett 1998, 640.
25. (d) Keller, E.; Feringa, B. L. Synlett 1997, 842.
26. (e) Akiyama, T.; Iwai, J. Tetrahedron Lett. 1997, 38, 853.
27. (f) Arai, Y.; Masuda, T.; Masaki, Y. Synlett 1997, 1459.
28. Yu, L.-B.; Chen, D.-P.; Wang, P. G. Tetrahedron Lett. 1996, 37, 2169.
29. Chen, D.; Yu, L.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467.
30. Yu, L.-B.; Chen, D.; Li, J.; Ramirez, J.; Wang, P. G. J. Org. Chem. 1997, 62, 208.
31. Yu, L.-B.; Li, J.; Ramirez, J.; Chen, D.; Wang, P. G. J. Org. Chem. 1997, 62, 903.
32. Yu, L.-B.; Li, J.; Chen, D.; Wang, P. G. J. Org. Chem. 1997, 62, 3575.
33. (a) Xie, W.-H.; Yu, L.-B.; Chen, D.-P.; Li, J.; Ramirez, J.; Wang, P. G. Green Chemistry : Frontiers in Benign Chemical Synthesis and Processes; Anastas, P. T., Williamson, T., Eds., Oxford University Press. 1998, p129.
34. (b) Organic Synthesis in Water Grieco, P. A., Ed., Blackie Academic & Professional: Hampshire, 1998.
35. (c) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media, John Wiley & Sons: New York, 1997.
36. 3. However, only common non-protic solvents were used:
37. (a) Rasmussen, K. G.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 1 1997, 1287.
38. (b) Nagayama, S.; Kobayashi, S. Chem. Lett. 1998, 685.
39. Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049.
40. Goh, S. H. J. Chem. Soc. (C) 1971, 2275.