Electrochemical Imination of Sulfoxides Using N-Aminophthalimide

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1839-1842

  Siu, Tung ^a   Yudin, Andrei K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; IMINE; N AMINOPHTHALIMIDE; N-AMINOPHTHALIMIDE; PHTHALIMIDE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; OXIDATION REDUCTION REACTION; SYNTHESIS;

ELECTROCHEMISTRY; ELECTRON TRANSPORT; IMINES; INDICATORS AND REAGENTS; OXIDATION-REDUCTION; PHTHALIMIDES; SULFOXIDES;

EID: 0037198779     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0257530     Document Type: Article

References (51)

1. (a) Bentley, H. R.; McDermott, E. E.; Pace. J.; Whitehead, J. K.; Moran, T. Nature 1950, 165.
2. (b) Whitehead, J. R.; Bentley, H. R. J. Chem. Soc. 1952, 1572.
3. (a) Griffith, O. W.; Meister, A. J. Biol. Chem. 1979, 254, 7558.
4. (b) Bailey, H. H. Chem.-Biol. Interact. 1998, 8, 23.
5. O'Dwyer, P. J.; Hamilton, T. C.; LaCreta, F. P.; Gallo, J. M.; Kilpatrick, D.; Halbherr, T.; Brennan, J.; Bookman, M. A.; Hoffman, J.; Young, R. C.; Comis, R. L.; Ozols, R. F. J. Clin. Oncol. 1996, 14, 249.
6. Mueller, E. Sulfoximines; German Patent 3,129,444, 1984.
7. Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.
8. For reviews on sulfoximine chemistry, see: (a) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1975, 4, 189. (b) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (c) Johnson, C. R. Aldrichimica Acta 1985, 18, 3. (d) Pyne, S. G. Sulfur Rep. 1992, 12, 57. (e) Reggelin, M.; Zur, C. Synthesis 2000, 1.
9. For reviews on sulfoximine chemistry, see: (a) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1975, 4, 189. (b) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (c) Johnson, C. R. Aldrichimica Acta 1985, 18, 3. (d) Pyne, S. G. Sulfur Rep. 1992, 12, 57. (e) Reggelin, M.; Zur, C. Synthesis 2000, 1.
10. For reviews on sulfoximine chemistry, see: (a) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1975, 4, 189. (b) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (c) Johnson, C. R. Aldrichimica Acta 1985, 18, 3. (d) Pyne, S. G. Sulfur Rep. 1992, 12, 57. (e) Reggelin, M.; Zur, C. Synthesis 2000, 1.
11. For reviews on sulfoximine chemistry, see: (a) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1975, 4, 189. (b) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (c) Johnson, C. R. Aldrichimica Acta 1985, 18, 3. (d) Pyne, S. G. Sulfur Rep. 1992, 12, 57. (e) Reggelin, M.; Zur, C. Synthesis 2000, 1.
12. For reviews on sulfoximine chemistry, see: (a) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1975, 4, 189. (b) Kennewell, P. D.; Taylor, J. B. Chem. Soc. Rev. 1980, 9, 477. (c) Johnson, C. R. Aldrichimica Acta 1985, 18, 3. (d) Pyne, S. G. Sulfur Rep. 1992, 12, 57. (e) Reggelin, M.; Zur, C. Synthesis 2000, 1.
13. Trost, B. M.; Matsuoka, R. T. Synlett 1992, 27.
14. (a) Johnson, C. R.; Haake, M.; Schroeck, C. W. J. Am. Chem. Soc. 1970, 92, 6594.
15. (b) Stoss, P.; Satzinger, G. Angew. Chem., Int. Ed. Engl. 1971, 10, 76.
16. (c) Rynbrandt, R. H.; Balgoyen, D. P. J. Org. Chem. 1978, 43, 1824.
17. (a) Ohashi, T.; Masunaga, K.; Okahara, M.; Komori, S. Synthesis 1971, 96.
18. (b) Colonna, S.; Stirling, C. J. M. J. Chem. Soc., Perkin Trans. 1 1974, 2120.
19. (c) Kim, M.; White, J. D. J. Am. Chem. Soc. 1977, 99, 1172.
20. (d) Kemp, J. E. G.; Closier, M. D.; Stefanich, M. H. Tetrahedron Lett. 1979, 3785.
21. (a) Kwart, H.; Kahn, A. A. J. Am. Chem. Soc. 1967, 89, 1950.
22. (b) Tanaka, R.; Yamabe, K. J. Chem. Soc., Chem. Commun. 1983, 329.
23. (a) Muller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805.
24. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116.
25. (a) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015.
26. (b) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033.
27. (a) Tamura, Y.; Sumoto, K.; Minamikawa, J.; Ikeda, M. Tetrahedron Lett. 1972, 4137.
28. (b) Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458.
29. (c) Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1.
30. (a) Claus, P. K.; Rieder, W.; Hofbauer, P.; Vilsmaier, E. Tetrahedron 1975, 31, 505.
31. (b) Heintzelman, R. W.; Bailey, R. B.; Swern, D. J. Org. Chem. 1976, 41, 2207.
32. Bard, A. J.; Faulkner, L. K. Electrochemical Methods: Fundamentals and Applications, Ed. 2; John Wiley & Sons: New York, 2001; Chapter 1.
33. (a) Lund, H.; Baizer, M. M. Organic Electrochemistry: An Introduction and a Guide, Ed. 3; M. Dekker: New York, 1991.
34. (b) Shono, T. Electroorganic Chemistry as a New Tool in Organic Synthesis; Springer-Verlag: New York, 1984.
35. (c) Torii, S., Ed. Novel Trends in Electroorganic Synthesis; Springer-Verlag: New York, 1998.
36. (d) Little, R. D.; Norman, L. Electroorganic Synthesis; M. Dekker: New York, 1991.
37. Steckhan, E.; Arns, T.; Heineman, W. R.; Hilt, G.; Hoormann, D.; Jorissen, J.; Kroner, L.; Lewall, B.; Putter, H. Chemosphere 2001, 43, 63.
38. Siu, T.; Yudin, A. K. J. Am. Chem. Soc. 2002, 124, 530.
39. Attempted oxidative imination of sulfides (resulting in sulfimines) using the same methodology was not successful. Due to the less positive oxidation potential of sulfides compared to N-aminophthalimide, a mixture of products consisting mainly of sulfoxide and sulfoximine was obtained.
40. For preparation of enantiomerically enriched sulfoxide, see: Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529.
41. 2 = 1.022.
42. (a) Whitehead, J. K.; Bentley, H. R. J. Chem. Soc. 1950, 2081.
43. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418.
44. (c) Hambley, T. W.; Raguse, B.; Ridley, D. D. Aust. J. Chem. 1986, 39, 1833.
45. (d) Kawanishi, H.; Morimoto, H.; Nakano, T.; Miyajima, T.; Oda, K.; Takeda, K.; Yano, S.; Hirano, N.; Tsujihara, K. Heterocycles 1998, 49, 169.
46. Johnson, C. R.; Lavergne, O. J. Org. Chem. 1989, 54, 986.
47. Bolm, C.; Muniz, K.; Aguilar, N.; Kesselgruber, M.; Raabe, G. Synthesis 1999, 1251.
48. (a) Siu, T.; Li, W.; Yudin, A. K. J. Comb. Chem. 2000, 2, 545.
49. (b) Siu, T.; Yekta, S.; Yudin, A. K. J. Am. Chem. Soc. 2000, 122, 11787.
50. (c) Yudin, A. K.; Siu, T. Curr. Opin. Chem. Biol. 2001, 5, 269.
51. (d) Siu, T.; Li, W.; Yudin, A. K. J. Comb. Chem. 2001, 3, 554.