Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: Synthesis of cyclic cis-vicinal diamines

Chemical Communications

Volumn , Issue 43, 2005, Pages 5402-5404

  Ebran, Jean Philippe ^a   Hazell, Rita G ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE; NITRONE DERIVATIVE; PROTON; SAMARIUM DIIODIDE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PINACOL REARRANGEMENT; SYNTHESIS;

EID: 28044469658     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b511491h     Document Type: Article

References (30)

1. For a review on the chemistry of vicinal diamines, see: D. Lucet, T. Le Gall and C. Mioskowski, Angew. Chem, Int. Ed., 1998, 37, 2580.
2. G. Fraenkel and P. Pramanik, J. Org. Chem., 1984, 49, 1316.
3. P. Gmeiner and E. Hummel, Synthesis, 1994, 1026.
4. (a) M. A. Sturgess and D. J. Yarberry, Tetrahedron Lett., 1993, 34, 4743;
5. (b) K. S. Feldman and J. C. Saunders, J. Am. Chem. Soc., 2002, 124, 9060.
6. W. Zhang and E. N. Jacobsen, Tetrahedron Lett., 1991, 32, 1711.
7. G. L. J. Bar, G. C. Lloyd-Jones and K. I. Booker-Milburn, J. Am. Chem. Soc., 2005, 127, 7308.
8. (a) N. Kise, H. Oide, E. Okazaki, M. Yoshimoto and T. Shono, J. Org. Chem., 1995, 60, 3980;
9. (b) R. Annunziata, M. Benaglia, M. Caporale and L. Raimondi, Tetrahedron: Asymmetry, 2002, 13, 2727.
10. (a) G. Masson, S. Py and Y. Vallée, Angew. Chem., Int. Ed., 2002, 41, 1772;
11. (b) M. Chavarot, M. Rivard, F. Rose-Munch, E. Rose and S. Py, Chem Commun., 2004, 2330;
12. (c) G. Masson, C. Philouze and S. Py, Org. Biomol. Chem., 2005, 3, 2067.
13. (a) D. Ribber and T. Skrydstrup, Org. Lett., 2003, 5, 229;
14. (b) S. A. Johannesen, S. Albu, R. G. Hazell and T. Skrydstrup, Chem. Commun., 2004, 1962.
15. (a) G. Masson, P. Cividino, S. Py and Y. Vallée, Angew. Chem., Int. Ed., 2003, 42, 2265;
16. (b) S. Desvergnes, S. Py and Y. Vallée, J. Org. Chem., 2005, 70, 1459.
17. Y.-W. Zhong, M.-H. Xu and G.-Q. Lin, Org. Lett., 2004, 6, 3953.
18. For recent reviews on the application of SmI2 in organic synthesis, see: (a) H. Kagan, Tetrahedron, 2003, 59, 10351;
19. (b) D. J. Edmonds, D. Johnston and D. J. Procter, Chem. Rev., 2004, 104, 3371;
20. (c) P. G. Steel, J. Chem. Soc., Perkin Trans. 1, 2001, 2727;
21. (d) G. A. Molander and C. R. Harris, Tetrahedron, 1998, 54, 3321;
22. (e) A. Krief and A.-M. Laval, Chem. Rev., 1999, 99, 745.
23. (a) C. F. Sturino and A. G. Fallis, J. Am. Chem Soc., 1994, 116, 7447;
24. (b) A. Fallis and I. M. Brinza, Tetrahedron, 1997, 53, 17543 and references cited therein;
25. (c) D. Riber, R. Hazell and T. Skrydstrup, J. Org. Chem, 2000, 65, 5382.
26. (a) K. C. Nicolaou, P. B. Rao, J. Hao, M. V. Reddy, G. Rassias, X. Huang, D. Y.-K. Chen and S. A. Snyder, Angew. Chem., Int. Ed., 2003, 42, 1753;
27. (b) I. Storch de Gracia, S. Bobo, M. D. Martìn-Ortega and J. L. Chiara, Org. Lett., 1999, 1, 1705 and references cited therein;
28. (c) H. Miyabe, M. Torieda, K. Inoue, K. Tajiri, T. Kiguchi and T. Naito, J. Org. Chem., 1998, 63, 4397.
29. A strong NOE was observed between the methyl group of 9i and the two protons of the urea group [Diagram presented]
30. For a detailed discussion see ref. 12 and references cited therein.