Efficient ring opening reactions of N-tosyl aziridines with amines and water in presence of catalytic amount of cerium(IV) ammonium nitrate

Chemistry Letters

Volumn 32, Issue 1, 2003, Pages 82-83

  Chakraborty, Tushar K ^a   Ghosh, Animesh ^a   Raju, T Venugopal ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMINOALCOHOL; AMMONIUM NITRATE; AZIRIDINE DERIVATIVE; BENZYLAMINE DERIVATIVE; CERIUM; METHYLAMINE; NITRIC ACID DERIVATIVE; WATER;

ARTICLE; CATALYSIS; STEREOCHEMISTRY;

EID: 0037419588     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.82     Document Type: Article

References (26)

1. For some recent reviews on aziridines see: a) R. S. Atkinson, Tetrahedron, 55, 1519 (1999). b) H. M. I. Osborn and J. Sweeney, Tetrahedron: Asymmetry, 8, 1693 (1997).
2. For some recent reviews on aziridines see: a) R. S. Atkinson, Tetrahedron, 55, 1519 (1999). b) H. M. I. Osborn and J. Sweeney, Tetrahedron: Asymmetry, 8, 1693 (1997).
3. B. A. Bhanu Prasad, R. Sanghi, and V. K. Singh, Tetrahedron, 58, 7355 (2002).
4. R. V. Anand, G. Pandey, and V. K. Singh, Tetrahedron Lett., 43, 3975 (2002).
5. C. Xiong, W. Wang, C. C. Cai, and V. J. Hruby, J. Org. Chem., 67, 1399 (2002).
6. J. E. W. Scheuermann, G. Ilyashenko, D. V. Griffiths, and M. Watkinson, Tetrahedron: Asymmetry, 13, 269 (2002).
7. I. A. O'Neil, J. C. Woolley, J. M. Southern, and H. Hobbs, Tetrahedron Lett., 42, 8243 (2002).
8. B. J. Paul, E. Hobbs, P. Buccino, and T. Hudlicky, Tetrahedron Lett., 42, 6433 (2001).
9. G. Sabitha, R. S. Babu, M. Rajkumar, C. S. Reddy, and J. S. Yadav, Tetrahedron Lett., 42, 3955 (2001).
10. B. J. Paul, T. A. Martinot, J. Wills, and T. Hudlicky, Synthesis, 2001, 952.
11. M. Chandrasekhar, G. Sekar, and V. K. Singh, Tetrahedron Lett., 41, 10079 (2000).
12. J. Wu, X.-L. Hou, and L.-X. Dai, J. Org. Chem., 65, 1344 (2000).
13. G. Sekar and V. K. Singh, J. Org. Chem., 64, 2537 (1999).
14. M. Meguro and Y. Yamamoto, Heterocycles, 43, 2473 (1996).
15. W.-H. Leung, M.-T. Yu, M.-C. Wu, and L.-L. Yeung, Tetrahedron Lett., 37, 891 (1996).
16. M. Meguro, N. Asao, and Y. Yamamoto, Tetrahedron Lett., 35, 7395 (1994).
17. H. M. I. Osborn and J. B. Sweeney, Synlett, 1994, 145.
18. S. Matsubara, T. Kodama, and K. Utimoto, Tetrahedron Lett., 31, 6379 (1990).
19. D. S. Jones, A. Srinivasan, S. Kasina, A. R. Fritzberg, and D. W. Wilkening, J. Org. Chem., 54, 1940 (1989).
20. V. Nair, V. Sheeba, S. B. Panicker, T. G. George, R. Rajan, L. Balagopal, M. Vairamani, and S. Prabhakar, Tetrahedron, 56, 2461 (2000).
21. V. Nair and T. G. George, Tetrahedron Lett., 41, 3199 (2000).
22. While our manuscript was under preparation, another paper appeared on CAN-catalyzed opening of aziridines with water: S. Chandrasekhar, Ch. Narsihmulu, and S. S. Sultana, Tetrahedron Lett., 43, 7361 (2002).
23. T. K. Chakraborty and G. V. Reddy, Tetrahedron Lett., 32, 679 (1991) and the references cited therein.
24. J. Cavanagh, W. J. Fairbrother, A. G. Palmer, III, and N. J. Skelton, "Protein NMR Spectroscopy," Academic Press, San Diego (1996).
25. K. Wüthrich, "NMR of Proteins and Nucleic Acids," Wiley, New York (1986).
26. A. V. Rama Rao, T. G. Murali Dhar, T. K. Chakraborty, and M. K. Gurjar, Tetrahedron Lett., 29, 2069 (1988).