A new selena-aza-payne-type rearrangement of aziridinylmethyl tosylates mediated by tetraselenotungstate

European Journal of Organic Chemistry

Volumn , Issue 27, 2007, Pages 4543-4551

  Sureshkumar, Devarajulu ^a   Koutha, Srinivasamurthy ^a   Chandrasekaran, Srinivasan ^a,b  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Allylamines; Aza payne rearrangement; Aziridines; Cyclic diselenides; Selenium nucleophiles

Indexed keywords

EID: 34748823696     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700357     Document Type: Article

References (33)

1. a) G. J. Payne, J. Org. Chem. 1962, 27, 3819-3822;
2. b) K. B. Sharpless, C. H. Behrens, T. Katsuki, A. W. Lee, V. S. Martin, M. Takatani, S. M. Viti, F. J. Walker, S. S. Woodard, Pure Appl. Chem. 1983, 55, 589-604;
3. c) R. M. Hanson, in Organic Reactions (Eds.: L. E. Overman), John Wiley & Sons, New York, 2002, vol. 60, p. 1-156.
4. T. Ibuka, Chem. Soc. Rev. 1998, 27, 145-154 and references cited therein.
5. J. K. Branalt, I. Kvarnstrom, J. Org. Chem. 1996, 61, 3604-3610.
6. G. Polson, D. C. Dittmer, J. Org. Chem. 1988, 53, 791-794.
7. a) A. S. Pepito, D. C. Dittmer, J. Org. Chem. 1997, 62, 7920-7925;
8. b) B. Chao, D. C. Dittmer, Tetrahedron Lett. 2001, 42, 5789-5791.
9. a) A. Dureault, C. Greek, J. C. Dpezay, Tetrahedron Lett. 1986, 27, 4157-4160;
10. b) J. Legters, L. Thijs, B. Zwanenburg, Tetrahedron Lett. 1989, 30, 4881-4884;
11. c) M. Haddach, R. Pastor, J. G. Riess, Tetrahedron Lett. 1990, 31, 1989-1990;
12. d) M. Hashimoto, K. Yamada, S. Terashima, Chem. Lett. 1992, 975-978.
13. D. Sureshkumar, S. Koutha, S. Chandrasekaran, J. Am. Chem. Soc. 2005, 127, 12760-12761.
14. a) V. Saravanan, E. Porhiel, S. Chandrasekaran, Tetrahedron Lett. 2003, 44, 2257-2260;
15. b) R. G. Bhat, E. Porhiel, V. Saravanan, S. Chandrasekaran, Tetrahedron Lett. 2003, 44, 5251-5253;
16. c) S. O'Neal, J. S. Kollis, J. Am. Chem. Soc. 1998, 110, 1971-1973;
17. d) A. Muller, E. Diemann, R. Jostes, H. Bogge, Angew. Chem. Int. Ed. Engl. 1981, 20, 934-955.
18. D. Sureshkumar, T. Gunasundari, V. Saravanan, S. Chandrasekaran, Tetrahedron Lett. 2007, 48, 623-626.
19. T. Axenrod, C. Watnick, H. Yazdekhasti, J. Org. Chem. 1995, 60, 1959-1964.
20. a) N. Kurose, T. Takahashi, T. Koizumi, J. Org. Chem. 1996, 61, 2932-2933;
21. b) S. Robin, G. Rousseau, Eur. J. Org. Chem. 2000, 3007-3011.
22. J. U. Jeong, B. Tao, I. Sagasser, H. Henniges, K. B. Sharpless, J. Am. Chem. Soc. 1998, 120, 6844-6845.
23. 2 = 0.158, GOF = 1.005, restrained GOF = 1.005 for all data.
24. 2 = 0.104, GOF =1.013, restrained GOF = 1.013 for all data.
25. a) P. M. Boorman, M. Wang, M. Parvez, J. Chem. Soc. Chem. Commun. 1995, 999-1000;
26. b) N. L. Kruhlak, M. Wang, P. M. Boorman, M. Parvez, Inorg. Chem. 2001, 40, 3141-3148;
27. c) K. R. Prabhu, N. Devan, S. Chandrasekaran, Synlett 2002, 1762-1778.
28. a) P. Lin, K. Bellos, H. Stamm, A. Onistschenko, Tetrahedron 1992, 48, 2359-2372;
29. b) D. Tanner, Angew. Chem. Int. Ed. Engl. 1994, 33, 599-619;
30. c) H. Stamm, J. Prakt. Chem. 1999, 341, 319-331;
31. d) F. A. Davis, W. McCoull, Synthesis 2000, 1347-1365;
32. e) X. E. Hu, Tetrahedron 2004, 60, 2701-2743;
33. f) P. Li, E. M. Forbeck, C. D. Evans, M. M. Joullie, Org. Lett. 2006, 8, 5105-5107.