Allylic disulfide rearrangement and desulfurization: Mild, electrophile-free thioether formation from thiols

Organic Letters

Volumn 8, Issue 16, 2006, Pages 3593-3596

  Crich, David ^a   Brebion, Franck ^a   Krishnamurthy, Venkataramanan ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; PEPTIDE; SULFIDE; THIOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; DISULFIDES; MOLECULAR STRUCTURE; PEPTIDES; SULFHYDRYL COMPOUNDS; SULFIDES;

EID: 33747305856     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061381+     Document Type: Article

References (44)

1. Crich, D.; Krishnamurthy, V.; Hutton, T. K. J. Am. Chem. Soc. 2006, 128, 2544.
2. (a) Höfle, G.; Baldwin, J. E. J. Am. Chem. Soc. 1971, 93, 6307.
3. (b) Baechler, R. D.; Hummel, J. P.; Mislow, K. J. Am. Chem. Soc. 1973, 95, 4442.
4. (c) Block, E.; Iyer, R.; Grisoni, S.; Saha, C.; Belman, S.; Lossing, F. P. J. Am. Chem. Soc. 1988, 110, 7813.
5. (d) Kutney, G. W.; Turnbull, K. Chem. Rev. 1982, 82, 333.
6. (e) Moore, C. G.; Trego, G. R. Tetrahedron 1962, 18, 205.
7. (f) Evans, M. B.; Higgins, G. M. C.; Moore, C. G.; Porter, M.; Saville, B.; Smith, J. F.; Trego, B. R.; Watson, A. A. Chem. Ind. 1960, 897.
8. (g) Pilgram, K.; Phillips, D. D.; Korte, F. J. Org. Chem. 1964, 29, 1844.
9. (a) Harano, K.; Taguchi, T. Chem. Pharm. Bull. 1972, 20, 2348.
10. (b) Harano, K.; Taguchi, T. Chem. Pharm. Bull. 1972, 20, 2357.
11. (c) Harano, K.; Taguchi, T. Chem. Pharm. Bull. 1975, 23, 467.
12. (d) Harano, K.; Ohizumi, N.; Hisano, T. Tetrahedron Lett. 1985, 26, 4203.
13. (e) Nakai, T.; Ari-Izumi, A. Tetrahedron Lett. 1976, 17, 2335.
14. (f) Nakai, T.; Mimura, T.; Ari-Izumi, A. Tetrahedron Lett. 1977, 18, 2425.
15. (g) Ueno, Y.; Sano, H.; Okawara, M. Tetrahedron Lett. 1980, 21, 1767.
16. (a) Talgoy, M. M.; Bell, A. W.; Duckworth, H. W. Can. J. Biochem. 1979, 57, 822.
17. (b) Kimura, T.; Matsueda, R.; Nakagawa, Y.; Kaiser, E. T. Anal. Biochem. 1982, 122, 274.
18. For examples of preparation of benzothiazolyl disulfides and pyridyl disulfides as well as their application to the synthesis of mixed disulfides, see: (a) Brzezinska, E.; Ternay, A. L. J. Org. Chem. 1994, 59, 8239.
19. (b) Rabanal, F.; DeGrado, W. F.; Dutton, P. L. Tetrahedron Lett. 1996, 37, 1347.
20. (c) Stoner, E. J.; Negrón, G.; Gaviño, R. In Handbook of Reagents for Organic Synthesis: Reagents for Glycoside, Nucleotide and Peptide Synthesis; Crich, D., Ed.; Wiley: London, 2005; p 330.
21. (d) Lundblad, R. L. Chemical Reagents for Protein Modification, 3rd ed.; CRC Press: Boca Raton, 2005.
22. Bisulfides 5-10 were kept at 0 °C for several. months with no evidence of rearrangement or degradation.
23. Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem., Int. Ed. 2004, 43, 828.
24. (a) Watson, A. A. J. Chem. Soc. (C) 1964, 2100.
25. (b) Morrison, N. J. J. Chem. Soc., Perkin Trans. 1 1984, 101.
26. Braverman, S.; Pechenick, T. Tetrahedron Lett. 2002, 43, 499.
27. Only traces of allylic sulfide 13, arising from the [2,3]-rearrangement with loss of sulfur, were identified by NMR.
28. 3, the disulfide 12 partially rearranged to allylic sulfide 13, even in the absence of phosphine.
29. 3OD, with no deuterium incorporation.
30. Light-induced alkene isomerization by diselenide. Barrett, A. G. M.; Barton, D. H. R.; Johnson, G.; Nagubandi, S. Synthesis 1978, 741.
31. Stereoselectivity of the allylic sulfoxide rearrangement. Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.
32. Stereoselectivity of [2,3]-Wittig rearrangement: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885.
33. (b) Nakai, T.; Mikami, K. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1994; Vol. 46, p 105.
34. (c) Mikami, K.; Nakai, T. Synthesis 1991, 594.
35. For example: (a) Ludolph, B.; Eisele, F.; Waldmann, H. J. Am. Chem. Soc. 2002, 124, 5954.
36. (b) Zhu, Y.; Van Der Donk, W. A. Org. Lett. 2001, 3, 1189.
37. (c) Cohen, S. B.; Halcomb, R. L. J. Am. Chem. Soc. 2002, 124, 2534.
38. (d) Galonic, D. P.; Ide, N. D.; Van Der Donk, W. A.; Gin, D. Y. J. Am. Chem. Soc. 2005, 127, 7359.
39. (e) Durek, T.; Alexandrov, K.; Goody, R. S.; Hildebrand, A.; Heinemann, I.; Waldmann, H. J. Am. Chem. Soc. 2004, 126, 16368.
40. (f) Kragol, G.; Lumbierres, M.; Palomo, J. M.; Waldmann, H. Angew. Chem., Int. Ed. 2004, 43, 5839.
41. (g) Thayer, D. A.; Yu, H. N.; Galan, M. C.; Wong, C.-H. Angew. Chem., Int. Ed. 2005, 44, 4596.
42. (h) Pachamuthu, K.; Zhu, X.; Schmidt, R. R. J. Org. Chem. 2005, 70, 3720.
43. (i) Palomo, J. M.; Lumbierres, M.; Waldmann, H. Angew. Chem., Int. Ed. 2006, 45, 477.
44. (j) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265.