Zn(ii)-catalyzed desymmetrization of meso-epoxides by aromatic amines in water

Synlett

Volumn , Issue 10, 2008, Pages 1574-1578

  Bonollo, Simona ^a   Frineuelli, Francesco ^a   Pizzo, Ferdinando ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

aqueous medium, aminolysis, meso epoxides, Zn(II) SDS, desymmetrization

Indexed keywords

AROMATIC AMINE; CYCLOHEXANE OXIDE; EPOXIDE; SCANDIUM; WATER; ZINC;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; REACTION ANALYSIS; SYNTHESIS;

EID: 46449125004     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078410     Document Type: Article

References (51)

1. (a) Organic Synthesis in Water, Lindström, U. M., Ed.; Blackwell: Oxford, 2007.
2. (b) Li, C.-J. Chem. Rev. 2005, 105, 3095.
3. (c) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
4. (d) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095.
5. (e) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Eur. J. Org. Chem. 2001, 439.
6. (f) Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic and Professional: London, 1998.
7. (g) Li, C. J.; Chang, T. H. In Organic Reactions in Aqueous Media; Wiley: New York, 1997.
8. (a) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Org. Lett. 2005, 7, 4411.
9. (b) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2004, 69, 2315.
10. (c) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Green Chem. 2003, 5, 436.
11. (d) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. J. Org. Chem. 2003, 68, 8248.
12. (e) Fringuelli, F.; Pizzo, F.; Rucci, M.; Vaccaro, L. J. Org. Chem. 2003, 68, 7041.
13. (a) Bonollo, S.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Synlett 2007, 2683.
14. (b) Bonollo, S.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2006, 8, 960.
15. (c) Wu, J.; Xia, H.-G. Green Chem. 2005, 7, 708.
16. (d) Surendra, K.; Krishnaveni, N. S.; Rao, K. R. Synlett 2005, 506.
17. (e) Azizi, M.; Saidi, M. R. Org. Lett. 2005, 7, 3649.
18. (a) Fioroni, G.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2003, 5, 425.
19. (b) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. J. Org. Chem. 2003, 68, 8248.
20. (c) Amantini, D.; Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Synlett 2003, 2292.
21. (d) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Tetrahedron Lett. 2001, 41, 1131.
22. (e) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2001, 3, 229.
23. (f) Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 4463.
24. (g) Fringuelli, F.; Pizzo, F.; Vaccaro, L. Synlett 2000, 311.
25. (a) Azoulay, S.; Manabe, K.; Kobayashi, S. Org. Lett. 2005, 7, 4593.
26. (b) Ogawa, C.; Wang, N.; Boudou, N.; Azoulay, S.; Manabe, K.; Kobayashi, S. Heterocylces 2007, 72, 589.
27. (a) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
28. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
29. (a) Corey, E. J.; Zhang, F. Angew. Chem. Int. Ed. 1999, 38, 1931.
30. (b) Johannes, C. W.; Visser, M. S.; Weatherhead, G. S.; Hoveyda, A. M. J. Am. Chem. Soc. 1998, 120, 8340.
31. (c) Chng, B. L.; Ganesan, A. Bioorg. Med. Chem. Lett. 1997, 7, 1511.
32. (d) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987.
33. (a) O'Brien, P. Angew. Chem. Int. Ed. 1999, 38, 326.
34. (b) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. Int. Ed. 1996, 35,451.
35. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
36. For recent examples, see: (a) Arai, K.; Lucarini, S.; Salter, M. M.; Ohta, K.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2007, 129, 8103.
37. (b) Arai, K.; Salter, M. M.; Yamashita, Y.; Kobayashi, S. Angew. Chem. Int. Ed. 2007, 46, 955.
38. (c) Mai, E.; Schneider, C. Chem. Eur. J. 2007, 13, 2729.
39. (d) Manabe, K.; Kobayashi, S. Heterocycles 2007, 72, 589.
40. (e) Mai, E.; Schneider, C. Synlett 2007, 2136.
41. (f) Kureshy, R. I.; Singh, S.; Khan, N. H.; Abdi, S. H. R.; Agrawal, S.; Jasra, R. V. Tetrahedron: Asymmetry 2006, 17, 1638.
42. (g) Schneider, C. Synthesis 2006, 3919.
43. (h) Kureshy, R. I.; Singh, S.; Khan, N. H.; Abdi, S. H. R.; Agrawal, S.; Mayani, V. J.; Jasra, R. V. Tetrahedron Lett. 2006, 47, 5277.
44. (i) Kureshy, R. I.; Singh, S.; Khan, N. H.; Abdi, S. H. R.; Suresh, E.; Jasra, R. V. Eur. J. Org. Chem. 2006, 1303.
45. (j) Carreé, F.; Gil, R.; Collin, J. Org. Lett. 2005, 7, 1023.
46. (k) Ogawa, C.; Wang, N.; Boudou, M.; Azoulay, S.; Ogawa, C.; Azoulay, S.; Kobayashi, S. Heterocycles 2005, 66, 201.
47. Handbook of Metal-Ligand Interactions in Biological Fluids; Berthon, G., Ed.; Marcel Dekker: New York/Basel/Hong Kong, 1995.
48. Suh, J. Acc. Chem. Res. 1992, 25, 273.
49. (a) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 102, 206;
50. Angew. Chem. 1990, 102, 206.
51. (b) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169.