Asymmetric oxidation of sulfides with H2O2 catalyzed by titanium complexes of Schiff bases bearing a dicumenyl salicylidenyl unit

Applied Organometallic Chemistry

Volumn 25, Issue 5, 2011, Pages 325-330

  Wang, Ying ^a   Wang, Mei ^a   Wang, Lin ^a   Wang, Yu ^a   Wang, Xiuna ^a   Sun, Licheng ^a,b  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

asymmetric catalysis; chiral sulfoxides; dicumenyl salicylaldehyde; Schiff bases; titanium

Indexed keywords

AMINO ALCOHOLS; ASYMMETRIC CATALYSIS; ASYMMETRIC OXIDATION; CATALYST LOADINGS; CHIRAL AMINO ALCOHOLS; CHIRAL INDUCTION; CHIRAL SULFOXIDES; DICUMENYL SALICYLALDEHYDE; GOOD YIELD; MOLAR RATIO; OPTIMAL CONDITIONS; SALICYLALDEHYDE; SCHIFF BASES; SCHIFF BASIS; SULFOXIDATION; TERMINAL OXIDANTS; TERT-BUTYL GROUP; THIOANISOLE; TITANIUM COMPLEXES;

ALCOHOLS; ALDEHYDES; AMINES; BEARINGS (STRUCTURAL); CATALYSIS; ENANTIOSELECTIVITY; FUNCTIONAL GROUPS; LIGANDS; ORGANIC POLYMERS; OXIDATION; TITANIUM;

TITANIUM COMPOUNDS;

EID: 79955012058     PISSN: 02682605     EISSN: 10990739     Source Type: Journal    
DOI: 10.1002/aoc.1762     Document Type: Article

References (53)

1. a) M. C. Carreño, Chem. Rev. 1995, 95, 1717
2. b) I. Fernández, N. Khiar, Chem. Rev. 2003, 103, 3651
3. c) H. Pellissier, Tetrahedron 2006, 62, 5559
4. d) V. G. Nenajdenko, A. L. Krasovskiy, E. S. Balenkova, Tetrahedron 2007, 63, 12481
5. e) E. Wojaczynska, J. Wojaczynski, Chem. Rev. 2010, 110, 4303.
6. a) H. Cotton, T. Elebring, M. Larsson, L. Li, H. Sörensen, S. von Unge, Tetrahedron: Asymmetry 2000, 11, 3819
7. b) A. Korte, J. Legros, C. Bolm, Synlett. 2004, 2397
8. c) J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. 2005, 347, 19
9. d) R. Bentley, Chem. Soc. Rev. 2005, 34, 609
10. e) Z. Han, J. J. Song, N. K. Yee, Y. Xu, W. Tang, J. T. Reeves, Z. Tan, X. Wang, B. Lu, D. Krishnamurthy, C. H. Senanayake, Org. Proc. Res. Devl. 2007, 11, 605.
11. a) P. Pitchen, H. B. Kagan, Tetrahedron Lett. 1984, 25, 1049
12. b) F. Di Furia, G. Modena, R. Seraglia, Synthesis 1984, 4, 325.
13. H. Cotton, T. Elebring, M. Larsson, L. Li, H. Sörensen, S. von Unge, Tetrahedron: Asymmetry 2000, 11, 3819.
14. a) O. Bortolini, F. Di Furia, G. Licini, G. Modena, M. Rossi, Tetrahedron Lett. 1986, 27, 6257
15. b) S. H. Zhao, O. Samuel, H. B. Kagan, Tetrahedron 1987, 43, 5135.
16. a) N. Komatsu, Y. Nishibayashi, T. Sugita, S. Uemura, Tetrahedron Lett. 1992, 33, 5391
17. b) N. Komatsu, M. Hashizume, T. Sugita, S. Uemure, J. Org. Chem. 1993, 58, 4529.
18. a) A. Colombo, G. Marturano, A. Pasini, Gazz. Chim. Ital. 1986, 116, 35
19. b) B. Saito, T. Katsuki, Tetrahedron Lett. 2001, 42, 3873.
20. K. P. Bryliakov, E. P. Talsi, Eur. J. Org. Chem. 2008, 3369.
21. a) Y. Yamanoi, T. Imamoto, J. Org. Chem. 1997, 62, 8560
22. b) M. I. Donnoli, S. Superchi, C. Rosini, J. Org. Chem. 1998, 63, 9392.
23. K. P. Bryliakov, E. P. Talsi, J. Mol. Catal. A: Chem. 2007, 264, 280.
24. M. Bonchio, G. Licini, F. Di Furia, S. Mantovani, G. Modena, W. A. Nugent, J. Org. Chem. 1999, 64, 1326.
25. a) M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett. 1992, 33, 7111
26. b) K. Noda, N. Hosoya, R. Irie, Y. Yamashita, T. Katsuki, Tetrahedron 1994, 50, 9609
27. c) T. Katsuki, Coord. Chem. Rev. 1995, 140, 189
28. d) M. Cavazzini, G. Pozzi, S. Quici, I. Shepperson, J. Mol. Catal. A: Chem. 2003, 204-205, 433.
29. a) C. Bolm, F. Bienewald, Angew. Chem. Int. Edn Engl. 1995, 34, 2640
30. b) N. N. Karpyshev, O. D. Yakovleva, E. P. Talsi, K. P. Bryliakov, O. V. Tolstikova, A. G. Tolstikov, J. Mol. Catal. A: Chem. 2000, 157, 91
31. c) J. Sun, C. Zhu, Z. Dai, M. Yang, Y. Pan, H. Hu, J. Org. Chem. 2004, 69, 8500
32. d) Y. C. Jeong, S. Choi, Y. D. Hwang, K. H. Ahn, Tetrahedron Lett. 2004, 45, 9249.
33. a) J. Legros, C. Bolm, Angew. Chem. Int. Ed. 2003, 42, 5487
34. b) J. Legros, C. Bolm, Angew. Chem. Int. Ed. 2004, 43, 4225
35. c) J. Legros, C. Bolm, Chem. Eur. J. 2005, 11, 1086.
36. a) T. Yamaguchi, K. Matsumoto, B. Saito, T. Katsuki, Angew. Chem. Int. Ed. 2007, 46, 4729
37. b) K. Matsumoto, T. Yamaguchi, J. Fujisaki, B. Saito, T. Katsuki, Chem. Asian. J. 2008, 3, 351
38. c) K. Matsumoto, T. Yamaguchi, T. Katsuki, Chem. Commum. 2008, 1704.
39. a) F. A. Davis, R. T. Reddy, M. C. Weismiller, J. Am. Chem. Soc. 1989, 111, 5964
40. b) F. A. Davis, R. T. Reddy, W. Han, P. J. Carroll, J. Am. Chem. Soc. 1992, 114, 1428
41. c) P. C. B. Page, J. P. Heer, D. Bethell, E. W. Collington, D. M. Andrews, Tetrahedron: Asymmetry 1995, 6, 2911
42. d) R. E. del Río, B. Wang, S. Achab, L. Bohé, Org. Lett. 2007, 9, 2265.
43. a) H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 8940
44. b) K. P. Bryliakov, E. P. Talsi, Chem. Eur. J. 2007, 13, 8045.
45. a) B. Pelotier, M. S. Anson, I. B. Campbell, S. J. F. Macdonald, G. Priem, R. F. W. Jackson, Synlett. 2002, 1055
46. b) C. Dargo, L. Caggiano, R. F. W. Jackson, Angew. Chem. Int. Ed. 2005, 44, 7221
47. c) A. Gao, M. Wang, D. Wang, L. Zhang, H. Liu, W. Tian, L. Sun, Chin. J. Catal. 2006, 27, 743
48. d) S. H. Hsieh, Y. P. Kuo, H. M. Gau, Dalton Trans. 2007, 97
49. e) Y. Wang, M. Wang, Y. Wang, X. Wang, L. Wang, L. Sun, J. Catal. 2010, 273, 177.
50. A. Gama, L. Z. Flores-Lõpez, G. Aguirre, M. Parre-Hake, R. Somanathan, P. J. Walsh, Tetrahedron: Asymmetry 2002, 13, 149.
51. S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2003, 68, 150.
52. M. J. McKennon, A. I. Meyers, K. Drauz, M. Schwarm, J. Org. Chem. 1993, 58, 3568.
53. R. Aldred, R. Johnston, D. Levin, J. Neilan, J. Chem. Soc. Perkin Trans I 1994, 13, 1823.