C-C bond-forming desulfurizations of sulfoximines

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4081-4084

  Reggelin, M ^a   Slavik, S ^c   Buhle P ^b  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b MERCK KGAA   (Germany)

^c GENERAL MOTORS CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; DRUG DERIVATIVE; METHIONINE SULFOXIMINE; SULFUR;

ARTICLE; CHEMISTRY;

CARBON; METHIONINE SULFOXIMINE; SULFUR;

EID: 55949092349     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8015995     Document Type: Article

References (44)

1. Bentley, H. R.; McDermott, E. E.; Pace, J.; Whitehead, J. K.; Moran, T. Nature 1949, 163, 675-676.
2. Gais, H. J. Heteroatom. Chem. 2007, 18, 472-481.
3. Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482-4-87.
4. Reggelin, M.; Zur, C. Synthesis 2000, 1-64.
5. Lu, S.-M.; Bolm, C. Adv. Synth. Catal. 2008, 350, 1101-1105.
6. Lemasson, F.; Gais, H. J.; Raabe, G. Tetrahedron Lett. 2007, 48, 8752-8756.
7. Spohr, V.; Kaiser, J. P.; Reggelin, M. Tetrahedron: Asymmetry 2006, 17, 500-503.
8. Reetz, M. T.; Bondarev, O. G.; Gais, H. J.; Bolm, C. Tetrahedron Lett. 2005, 46, 5643-5646.
9. Reggelin, M.; Weinberger, H.; Spohr, V. Adv. Synth. Catal. 2004, 346, 1295-1306.
10. Bolm, C.; Verrucci, M.; Simic, O.; Cozzi Pier, G.; Raabe, G.; Okamura, H. Chem Commun. 2003, 2826-2827.
11. Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427-429.
12. Bolm, C.; Simic, O.; Martin, M. Synlett 2001, 1878-1880.
13. Reggelin, M.; Junker, B. Chem. Eur. J. 2001, 7, 1232-1239.
14. (a) Reggelin, M.; Weinberger, H.; Gerlach, M.; Welcker, R. J. Am. Chem. Soc. 1996, 118, 4765-4777.
15. (b) Reggelin, M.; Weinberger, H. Angew. Chem., Int. Ed. 1994, 33, 444-446.
16. Reggelin, M.; Gerlach, M.; Vogt, M. Eur. J. Org. Chem. 1999, 1011-1031.
17. Reggelin, M.; Weinberger, H.; Heinrich, T. Liebigs Ann. Recl. 1997, 1881-1886.
18. (a) Reggelin, M.; Junker, B.; Heinrich, T.; Slavik, S.; Bühle, P. J. Am. Chem. Soc. 2006, 128, 4023-4034.
19. (b) Reggelin, M.; Heinrich, T. Angew. Chem., Int. Ed. 1998, 37, 2883-2886.
20. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467-3478.
21. Rich, D. H.; Ripka, A. S. Curr. Opin. Chem. Biol. 1998, 2, 441-452.
22. Reggelin, M.; Kühl, J.; Kaiser, J. P.; Bühle, P. Synthesis 2006, 2224-2232.
23. Nevertheless, with N-methyl-substituted sulfoximines this has been shown to be possible. Rajender, A.; Gais, H. J. Org. Lett. 2007, 9, 579-582.
24. Gais, H.-J.; Loo, R.; Roder, D.; Das, P.; Raabe, G. Eur. J. Org. Chem. 2003, 1500-1526.
25. Kohler, F.; Gais, H. J.; Raabe, G. Org. Lett. 2007, 9, 1231-1234.
26. Adrien, A.; Gais, H. J.; Kohler, F.; Runsink, J.; Raabe, G. Org. Lett. 2007, 9, 2155-2158.
27. (a) Zhou, Y. B.; Cao, F. L. J. Organomet. Chem. 2007, 692, 3723-3731.
28. (b) Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756.
29. Köbrich, G. Angew. Chem., Int. Ed. 1972, 11, 473-485.
30. Köbrich, G.; Von Nagel, R. Chem.-Ztg. 1970, 94, 984-985.
31. (a) Villieras, J. Bull. Soc. Chim. Fr. 1967, 1520-1532.
32. (b) Hahn, R. C.; Tompkins, J. Tetrahedron Lett. 1990, 31, 937-940.
33. (c) De Lima, C.; Julia, M.; Verpeaux, J. N. Synlett 1992, 133-134.
34. (d) Charreau, P.; Julia, M.; Verpeaux, J.-N. J. Organomet. Chem. 1989, 379, 201.
35. (a) Plietker, B.; Seng, D.; Fröhlich, R.; Metz, P. Eur. J. Org. Chem. 2001, 3669-3676.
36. (b) Plietker, B.; Metz, P. Tetrahedron Lett. 1998, 39, 7827-7830.
37. (c) Pearlman, B. A.; Putt, S. R.; Fleming, J. A. J. Org. Chem. 2006, 71, 5646-5657.
38. Reggelin, M.; Weinberger, H. Tetrahedron Lett. 1992, 33, 6959-6962.
39. Reggelin, M.; Welcker, R. Tetrahedron Lett. 1995, 36, 5885-5886.
40. Li, C.; Blackman, A. J. Aust. J. Chem. 1995, 48, 955-965.
41. Li, C.; Blackman, A. J. Aust. J. Chem. 1994, 47, 1355-1361.
42. Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645-8656.
43. Isaac, M.; Slassi, A.; O'Brien, A.; Edwards, L.; MacLean, N.; Bueschkens, D.; Lee, D. K. H.; McCallum, K.; De Lannoy, I.; Demchyshyn, L.; Kamboj, R. Bioorg. Med. Chem. Lett. 2000, 10, 919-921.
44. Black, D. S.; Kumar, N.; Mitchell, P. S. R. J. Org. Chem. 2002, 67, 2464-2473.