Enantioselective oxidation of di-tert-butyl disulfide with a vanadium catalyst: Progress toward mechanism elucidation

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 150-155

  Blum, Suzanne A ^a   Bergman, Robert G ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE OXIDATION;

CATALYSTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; VANADIUM;

AROMATIC COMPOUNDS;

DI TERT BUTYL DISULFIDE; DISULFIDE; LIGAND; SCHIFF BASE; SOLVENT; UNCLASSIFIED DRUG; VANADIUM;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION;

EID: 0037427992     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0205560     Document Type: Article

References (47)

1. Yang, T.-K.; Chen, R.-Y.; Lee, D.-S.; Jiang, Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem. 1994, 59, 914-921.
2. Moreau, P.; Essiz, M.; Mérour, J.-Y.; Bouzard, D. Tetrahedron: Asymmetry 1997, 8, 591-98.
3. Liu, G.; Cogan, D.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914.
4. Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans. 1 1982, 341-343.
5. Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13-18.
6. Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243-3245.
7. Ruano, J. L. G.; Fernández, I.; Catalina, M. D.; Cruz, A. A. Tetrahedron: Asymmetry 1996, 7, 3407-3414.
8. Davis, F. A.; Reddy, G. V.; Liang, C.-H. Tetrahedron Lett. 1997, 38, 5139-5142.
9. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J. Tetrahedron: Asymmetry 1997, 8, 3991-3994.
10. Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532-7533.
11. Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M. W.; Blaszczyk, J. J. Chem. Soc., Chem Commun. 1996, 1503-1504.
12. Andersen, K. K. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. H., Eds.; Jon Wiley & Sons: New York, 1988; pp 56-94.
13. Kagan, H. B.; Rebiere, F. Synlett 1990, 643-649.
14. Solladié, G. Synthesis 1981, 185-196.
15. Cogan, D.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011-8019.
16. Bolm, C.; Bienewald, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2640-2642.
17. Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. A 1997, 117, 347-350.
18. Owens, T. D.; Tang, T. P.; Ellman, J. A. Acc. Chem. Res. 2002, 35, 984-995.
19. Prakash, S. G. K.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589-590.
20. Cogan, D.; EIlman, J. A. J. Am. Chem. Soc. 1999, 121, 268-269.
21. Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12-13.
22. Adrio, J.; Carretero, J. C. J. Am. Chem. Soc. 1999, 121, 7411-7412.
23. Priego, J.; Carratero, J. C. Synlett 1999, 1603-1605.
24. Michaelson, R. C.; Palermo, R. E.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 1990-1992.
25. Hoshino, Y.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10452-10453.
26. Murase, N.; Hoshino, Y.; Oishi, M.; Yamamoto, H. J. Am. Chem. Soc. 1942, 64, 338-339.
27. Hoshino, Y.; Murase, N.; Oishi, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 2000, 73, 1653-1658.
28. Bolm, C.; Kühn, T. Synlett 2000, 899-901.
29. Traber, B.; Jung, Y.-G.; Park, T. K.; Hong, J.-I. Bull. Korean Chem. Soc 2001, 22, 547-548.
30. Colpas, G. J.; Hamstra, B. J.; Kampf, J. W.; Pecoraro, V. L. J. Am. Chem. Soc. 1996, 118, 3469-3478.
31. Clague, M. J.; Butler, A. J. Am. Chem. Soc. 1995, 117, 3475-3484.
32. Clague, M. J.; Keder, N. L.; Butler, A. Inorg. Chem. 1993, 32, 4754-4761.
33. Bortolini, O.; Carraro, M.; Conte, V.; Moro, S. Eur. J. Inorg. Chem. 1999, 1489-1495.
34. Süss-Fink, G.; Stanislas, S.; Shul'pin, G. B.; Nizova, G. V.; Stoeckli-Evans, H.; Neels, A.; Bobillier, C.; Claude, S. J. Chem. Soc., Dalton Trans. 1999, 3169-3175.
35. Süss-Fink, G.; Stanislas, S.; Shul'pin, G. B.; Nizova, G. V. Appl. Organomet. Chem 2000, 14, 623-628.
36. Karpyshev, N. N.; Yakovleva, O. D.; Talsi, E. P.; Bryliakov, K. P.; Tolstikova, O. V.; Tolstikov, A. G. J. Mol. Catal. A 2000, 157, 91-95.
37. Skarzewski, J.; Ostrycharz, E.; Siedlecka, R. Tetrahedron: Asymmetry 1999, 10, 3457-3461.
38. Bolm, C.; Bienewald, F. Synlett 1998, 1327-1328.
39. Schmidt, H.; Bashirpoor, M.; Rehder, D. J. Chem. Soc., Dalton Trans. 1996, 3865-3870.
40. Nakajima, K.; Kojima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1990, 63, 2620-2630.
41. Nakajima, K.; Kojima, M.; Toriumi, K.; Saito, K.; Fujita, J. Bull. Chem. Soc. Jpn. 1989, 62, 760-767.
42. Ohta, C.; Shimizu, H.; Kondo, A.; Katsuki, T. Synlett 2002, 161-163.
43. Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741-1744.
44. Skarzewski, J.; Ostrycharz, E.; Siedlecka, R.; Zielinska-Blajet, B.; Pisarski, J. J. Chem. Res. S 2001, 263-264.
45. Bryliakov, K. P.; Karpyshev, N. N.; Fominsky, S. S.; Tolstikov, A. G.; Talsi, E. P. J. Mol. Catal. A 2001, 171, 73-80.
46. Conte, V.; DiFuria, F.; Moro, S. J. Mol. Catal. A 1997, 117, 139-149.
47. Bienewald, F. In Entwicklung neuer Katalysatorsysteme fur asymmetrische Oxidationen. Ph.D. Thesis, Philipps-Universitat, Marburg, 1996.