Silver-catalyzed imination of sulfoxides and sulfides

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4983-4985

  Gae, Young Cho ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27644493286     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0519442     Document Type: Article

References (57)

1. For recent examples, see: (a) Bolm, C.; Simic, O. J. Am. Chem. Soc. 2001, 123, 3830.
2. (b) Harmata, M.; Ghosh, S. K. Org. Lett. 2001, 3, 3321.
3. (c) Bolm, C.; Martin, M.; Simic, O.; Verrucci, M. Org. Lett. 2003, 5, 427.
4. (d) Bolm, C.; Verrucci, M.; Simic, O.; Cozzi, P. G.; Raabe, G.; Okamura, H. Chem. Commun. 2003, 2816.
5. (e) Bolm, C.; Martin, M.; Gescheidt, G.; Palivan, C.; Neshchadin, D.; Bertagnolli, H.; Feth, M. P.; Schweiger, A.; Mitrikas, G.; Harmer, J. J. Am. Chem. Soc. 2003, 125, 6222.
6. (g) Langner, M.; Bolm, C. Angew. Chem., Int. Ed. 2004, 43, 5984.
7. Reviews: (h) Harmata, M. Chemtracts 2003, 16, 660.
8. (i) Reetz, M. T.; Bondarev, O. G.; Gais, H.-J.; Bolm, C. Tetrahedron Lett. 2005, 46, 5643.
9. (j) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482 and references therein.
10. (a) Bolm, C.; Kahmann, J. D.; Moll, G. Tetrahedron Lett. 1997, 38, 1169.
11. (b) Bolm, C.; Moll, G.; Kahmann, J. D. Chem. Eur. J. 2001, 7, 1118.
12. (c) Tye, H.; Skinner, C. L. Helv. Chim. Acta 2002, 85, 3272.
13. (d) Bolm, C.; Müller, D.; Hackenberger, C. P. R. Org. Lett. 2002, 4, 893.
14. (e) Bolm, C.; Müller, D.; Dalhoff, C.; Hackenberger, C. P. R.; Weinhold, E. Bioorg. Med. Chem. Lett. 2003, 13, 3207.
15. Reviews on sulfoximines and sulfilimines: (a) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.
16. (b) Pyne, S. G. Sulfur Rep. 1999, 21, 281.
17. (c) Taylor, P. C. Sulfur Rep. 1999, 21, 241.
18. (d) Reggelin, M.; Zur, C. Synthesis 2000, 1.
19. +: (a) Fusco, R.; Tericoni, F. Chim. Ind. (Milan) 1965, 47, 61.
20. (b) Johnson, C. R.; Schroeck, C. W. J. Am. Chem. Soc. 1973, 95, 7418
21. . (c) For an improved protocol, see: Brandt, J.; Gais, H.-J. Tetrahedron: Asymmetry 1997, 6, 909.
22. 3: Merck Index, 12th ed.; Budavari, S., Ed.; Merck & Co., Inc.: Rahway, NJ, 1996; p 451.
23. MSH: (a) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239.
24. (b) Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458.
25. (c) Tamura, Y.; Matushima, H.; Minamikawa, J.; Ikeda, M.; Sumoto, K. Tetrahedron 1975, 31, 3035.
26. (d) Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis; John Wiley & Sons: New York, 1975; Vol. 5; p 430.
27. For other metal-free sulfoxide iminations, see: (a) Use of electrochemistry: Siu, T.; Picard, C. J.; Yudin, A. K. J. Org. Chem. 2005, 70, 932.
28. (b) Krasnova, L. B.; Hili, R. M.; Chernoloz, O. V.; Yudin, A. K. Arkivoc 2005, iv, 26.
29. (c) Application of a rather unstable 3-acetoxyaminoquinazolinone (QNHOAc) as nitrogen source (which requires the use of toxic lead tetraacetate for its preparation): Karabuga, S.; Kazaz, C.; Kilic, H.; Ulukanli, S.; Celik, A. Tetrahedron Lett. 2005, 46, 5225.
30. Cu salts: (a) Müller, J. F. K.; Vogt, P. Tetrahedron Lett. 1998, 39, 4805.
31. (b) Lacôte, E.; Amatore, M.; Fensterbank, L.; Malacria, M. Synlett 2002, 116.
32. (c) Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H. Tetrahedron Lett. 2002, 43, 2749.
33. (d) Tomooka, C. S.; Carreira, E. M. Helv. Chim. Acta 2003, 85, 3773.
34. (e) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem., Int. Ed. 1999, 38, 1288.
35. Fe salts: (f) Bach, T.; Körber, C. Tetrahedron Lett. 1998, 39, 5015.
36. (g) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 64, 1033.
37. Mn complexes: (a) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937.
38. (b) Ohta, C.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3885.
39. Ru complexes: (c) Murakami, M.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 7071.
40. (d) Tamura, Y.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2003, 44, 3301.
41. (e) Murakami, M.; Uchida, T.; Saito, B.; Katsuki, T. Chirality 2003, 15, 116.
42. (f) Uchida, T.; Tamura, Y.; Ohba, M.; Katsuki, T. Tetrahedron Lett. 2003, 44, 7965.
43. Okamura, H.; Bolm, C. Org. Lett 2004, 6, 1305.
44. For selected examples, see: (a) Cui, Y.; He, C. J. Am. Chem. Soc. 2003, 125, 16202.
45. (b) Cui, Y.; He, C. Angew. Chem., Int. Ed. 2004, 43, 4210.
46. (c) Cirakovic, J.; Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 9370.
47. (d) Driver, T. G.; Woerpel, K. A. J. Am. Chem. Soc. 2004, 126, 9993.
48. (e) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018.
49. (f) Ji, J.-X.; Au-Yeung, T. T.-L.; Wu, J.; Yip, C. W.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 42.
50. (g) Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701.
51. (h) Yanagisawa, A.; Touge, T.; Arai, T. Angew. Chem., Int. Ed. 2005, 44, 1546.
52. 3tpy also proved useful in silver-catalyzed aziridinations and nitrene insertions as reported by Cui and He (compare ref 10b,c).
53. The microwave-assisted (200 W) silver-catalyzed imination of methyl phenyl sulfoxide (1a) led to sulfoximine 2 in 85% yield (unoptimized) after 20 min, and it occurred in a sterospecific manner.
54. R(S): 42.6 min.
55. Cleavage of the SES-group by treatment with TBAF is also well-established (compare ref 7c), and there is no indication that this protocol leads to racemization.
56. For a recent contribution on sulfodiimines, see: Dehli, J. R.; Bolm, C. Synthesis 2005, 1058.
57. 3 (Aldrich prices per gram in 2005).