Enantioselective oxidation of sulfides with hydrogen peroxide catalyzed by vanadium complex of sterically hindered chiral Schiff bases

Tetrahedron Letters

Volumn 45, Issue 50, 2004, Pages 9249-9252

  Jeong, Yong Chul ^a   Choi, Soojin ^a   Hwang, Yao Dong ^a   Ahn, Kwang Hyun ^a  

^a Kyung Hee University   (South Korea)

Author keywords

Chiral sulfoxide; Enantioselective sulfoxidation; Hydrogen peroxide

Indexed keywords

ALKYL GROUP; BENZENE DERIVATIVE; HYDROGEN PEROXIDE; LIGAND; SCHIFF BASE; SULFIDE; VANADIUM DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; MOLECULAR MECHANICS; OXIDATION KINETICS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 8544233507     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.070     Document Type: Article

References (38)

1. M.C. Carreno Chem. Rev. 95 1995 1717
2. F. Colobert, A. Tito, N. Khiar, D. Denni, M.A. Media, M. Martin-Lomas, J.-L. Ruano, and G. Solladie J. Org. Chem. 63 1998 8918
3. M.C. Carreno, M. Ribagorda, and G.H. Posner Angew. Chem., Int. Ed. 41 2002 2753
4. J.P. Marino, M.S. Mcclure, D.P. Holub, J.V. Comasseto, and F.C. Tucci J. Am. Chem. Soc. 124 2002 1664
5. M. Tanaka, H. Yamazaki, H. Hakusui, N. Nakamichi, and H. Sekino Chirality 9 1997 17
6. C.A. Hutton, and J.M. White Tetrahedron Lett. 38 1997 1643
7. H.L. Holland, and F.M. Brown Tetrahedron: Asymmetry 9 1998 535
8. H. Cotton, T. Elebring, M. Larsson, L. Li, H. Sorensen, and S. von Unge Tetrahedron: Asymmetry 11 2000 3819
9. K.-H. Ahn, H. Kim, J.R. Kim, S.C. Jeong, T.S. Kang, H.T. Shin, and G.J. Lim Bull. Korean Chem. Soc. 23 2002 626
10. P. Pitchen, M.N. Deshmukh, E. Duach, and H.B. Kagan J. Am. Chem. Soc. 106 1984 8188
11. F. Di Furia, G. Modena, and R. Seraglia Synthesis 1984 325
12. H.B. Kagan, and F. Rebiere Synlett 1990 643
13. N. Komatsu, Y. Nishibayashi, T. Sugita, and S. Uemura Tetrahedron Lett. 33 1992 5391
14. N. Komatsu, M. Hashizume, T. Sugita, and S. Uemura J. Org. Chem. 58 1993 4529
15. J.-M. Brunel, T.O. Luukas, and H.B. Kagan Tetrahedron: Asymmetry 9 1998 1941
16. M.I. Donnoli, S. Superchi, and C. Rosini J. Org. Chem. 63 1998 9392
17. M. Bonchio, G. Licini, G. Modena, O. Bortolini, S. Moro, and W.A. Nugent J. Am. Chem. Soc. 121 1999 6258
18. B. Saito, and T. Katsuki Tetrahedron Lett. 42 2001 3873
19. B. Saito, and T. Katsuki Tetrahedron Lett. 42 2001 8333
20. A. Massa, F.R. Siniscalchi, V. Bugatti, A. Lattanzi, and A. Scettri Tetrahedron: Asymmetry 13 2002 1277
21. M.A.M. Capozzi, C. Cardellicchio, F. Naso, and V. Rosito J. Org. Chem. 67 2002 7289
22. T. Tanaka, B. Saito, and T. Katsuki Tetrahedron Lett. 43 2002 3259
23. M. Palucki, P. Hanson, and E.N. Jacobsen Tetrahedron Lett. 33 1992 7111
24. K. Noda, N. Hosoya, R. Irie, Y. Yamashita, and T. Katsuki Tetrahedron 50 1994 9609
25. A. Chellamani, P. Kylanthaipandi, and S. Rajagopal J. Org. Chem. 64 1999 2232
26. J. Legros, and C. Bolm Angew. Chem., Int. Ed. 42 2003 5487
27. J. Legros, and C. Bolm Angew. Chem., Int. Ed. 43 2004 4225
28. K. Nakajima, K. Kojima, and J. Fujita J. Chem. Lett. 1986 1483
29. C. Bolm, and F. Binewald Angew. Chem., Int. Ed. Engl. 34 1995 2640
30. A.D. Cogan, G. Liu, K. Kim, B.J. Backes, and J.A. Ellman J. Am. Chem. Soc. 120 1998 8011
31. A.H. Vetter, and A. Berkessel Tetrahedron Lett. 39 1998 1741
32. C. Ohta, H. Shimizu, A. Kondo, and T. Katsuki Synlett 2002 161
33. B. Pelotier, M.S. Anson, I.B. Campbell, S.J.F. Macdonald, and G. Priem Synlett 2002 1055
34. C. Bolm Coord. Chem. Rev. 237 2003 245
35. J. Skarzewski, E. Ostrycharz, and R. Siedlecka Tetrahedron: Asymmetry 10 1999 3457
36. K.-H. Ahn, S.W. Park, S. Choi, H.-J. Kim, and C.J. Moon Tetrahedron Lett. 42 2001 2485
37. 2O: C, 74.54; H, 7.23; N, 2.72. Found C, 74.76; H, 6.85; N, 2.63%
38. 4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography