Investigations on the iron-catalyzed asymmetric sulfide oxidation

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1086-1092

  Legros, Julien ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Asymmetric amplification; Asymmetric catalysis; Iron; Oxidation; Sulfoxide

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; HYDROGEN PEROXIDE; IRON; OXIDATION; REACTION KINETICS;

CARBOXYLATE SALTS; ENANTIOSELECTIVITIES; SULFIDE OXIDATION; SULFOXIDE-TO-SULFONE OXIDATION;

SULFUR COMPOUNDS;

CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; HYDROGEN PEROXIDE; IRON; OXIDIZING AGENT; SULFIDE; SULFONE; SULFOXIDE;

AQUEOUS SOLUTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; OPTICAL ROTATION; OXIDATION; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; TECHNIQUE;

EID: 14544284520     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400857     Document Type: Article

References (69)

1. For reviews on the use of chiral sulfoxides, see: a) I. Fernández, N. Khiar, Chem. Rev. 2003, 103, 3651-3705;
2. b) M. C. Carreño, Chem. Rev. 1995, 95, 1717-1760.
3. a) A. Massa, A. V. Malkov, P. Kocovsky, A. Scettri, Tetrahedron Lett 2003, 44, 7179-7181;
4. b) S. Kobayashi, C. Ogawa, H. Konishi, M. Sugiura, J. Am. Chem. Soc. 2003, 125, 6610-6611.
5. One of the most sold drugs in the world (with total sales in 2002 of US$ 6.6 Billion) is the chiral sulfoxide Omeprazole. Its enantioselective synthesis involves an asymmetric sulfide oxidation, a) For a summary of recent developments and data, see: A. M. Rouhi, Chem. Eng. News 2003, 81(19), 56-61;
6. b) for a general overview on asymmetric syntheses of biologically active chiral sulfoxides, see: J. Legros, J. R. Dehli, C. Bolm, Adv. Synth. Catal. in press.
7. Reviews on asymmetric sulfoxidations: a) H. B. Kagan, T. Luukas in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, pp. 361-373;
8. b) H. B. Kagan in Catalytic Asymmetric Synthesis (Ed.: I. Ojima). 2nd ed., Wiley-VCH, New York, 2000, pp. 327-356;
9. c) C. Bolm, K. Muñiz, J. P. Hildebrand in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 697-713.
10. Recently, niobium and tungsten complexes have also been involved in asymmetric sulfoxidation reactions: a) Nb: T. Miyazaki, T. Katsuki, Synlett 2003, 1046-1048;
11. b) W. V. V. Takur, A. Sudalai, Tetrahedron: Asymmetry 2003, 14, 407-410.
12. For a general review on the use of iron catalysts in organic synthesis, see: C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254.
13. a) J. T. Groves, P. Viski, J. Org. Chem. 1990, 55, 3628-3634;
14. b) Y. Naruta, F. Tani, K. Maruyama, J. Chem. Soc. Chem. Commun. 1990, 1378-1380;
15. c) Y. Naruta, F. Tani, K. Maruyama, Tetrahedron: Asymmetry 1991, 2, 533-542;
16. d) L.-C. Chiang, K. Konishi, T. Aida, S. Inoue, J. Chem. Soc. Chem. Commun. 1992, 254-256;
17. e) Q. L. Zhou, K. C. Chen, Z. H. Zhu, J. Mol. Catal. 1992, 72, 59-65;
18. f) C. Duboc-Toia, S. Ménage, C. Lambeaux, M. Fontecave, Tetrahedron Lett. 1997, 38, 3727-3730;
19. g) C. Duboc-Toia, S. Ménage, R. Y. N. Ho, L. Que Jr., C. T. Lambeaux, M. Fontecave, Inorg. Chem. 1999, 38, 1261-1268;
20. h) Y. Mekmouche, H. Hummel, R. Y. N. Ho, L. Que Jr., V. Schünemann, F. Thomas, A. X. Trautwein, C. Lebrun, K. Gorgy, J.-C. Leprêtre, M.-N. Collomb, A. Deronzier, M. Fontecave, S. Ménage, Chem. Eur. J. 2002, 8, 1196-1204.
21. J. Legros, C. Bolm, Angew. Chem. 2003, 775, 5645-5647; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
22. J. Legros, C. Bolm, Angew. Chem. 2003, 775, 5645-5647; Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
23. 2: a) C. Bolm, F. Bienewald, Angew. Chem. 1995, 707, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642;
24. 2: a) C. Bolm, F. Bienewald, Angew. Chem. 1995, 707, 2883-2885; Angew. Chem. Int. Ed. Engl. 1995, 34, 2640-2642;
25. b) C. Bolm, G. Schlingloff, F. Bienewald, J. Mol. Catal. 1997, 777, 347-350;
26. c) C. Bolm, F. Bienewald, Synlett 1998, 34, 1327-1328;
27. d) B. Pelotier, M. S. Anson, I. B. Campbell, S. J. F. Macdonald, G. Priem, R. F. W. Jackson, Synlett 2002, 1055-1060;
28. e) C. Ohta, H. Shimizu, A. Kondo, T. Katsuki, Synlett 2002, 161-163;
29. f) S. A. Blum, R. G. Bergman, J. A. Ellman, J. Org. Chem. 2083, 68, 150-155;
30. g) D. J. Weix, J. A. Ellman, Org. Lett. 2003, 5, 1317-1320;
31. h) for a review, see: C. Bolm, Coord. Chem. Rev. 2003, 237, 245-256, and references therein.
32. For overviews on the use of hydrogen peroxide in oxidation reactions, see: a) Catalytic Oxidations with Hydrogen Peroxide as Oxidant (Ed.: G. Strukul), Kluwer Academic, Dordrecht, 1992;
33. b) C. W. Jones, Applications of Hydrogen Peroxides and Derivatives, Royal Society of Chemistry, Cambridge, 1999;
34. c) B. S. Lane, K. Burgess, Chem. Rev. 2003, 103, 2457-2473;
35. d) R. Noyori, M. Aoki, K. Sato, Chem. Commun. 2003, 1977-1986.
36. a) J. Legros, C. Bolm, Angew. Chem. 2004, 116, 4321-4324; Angew. Chem. Int. Ed. 2004, 43, 4225-4228;
37. a) J. Legros, C. Bolm, Angew. Chem. 2004, 116, 4321-4324; Angew. Chem. Int. Ed. 2004, 43, 4225-4228;
38. b) see also: A. Korte, J. Legros, C. Bolm, Synlett 2004, 2397-2399.
39. a) For an interesting list of additives used in metal-catalyzed epoxidations with hydrogen peroxide, see ref. [10c];
40. b) for a general review on additive effects in catalysis, see: E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 777, 1672-1680; Angew. Chem. Int. Ed. 1999, 38, 1570-1577.
41. b) for a general review on additive effects in catalysis, see: E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 777, 1672-1680; Angew. Chem. Int. Ed. 1999, 38, 1570-1577.
42. M. C. White, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 725, 7194-7195.
43. a) The vanadium-catalyzed asymmetric oxidations of 2a with Schiff bases 1a and 1b gave 3b with 90% (see ref. [9d]) and 60% ee, respectively. J. Legros, C. Bolm, unpublished results;
44. see also: D. A. Cogan, G. Liu, K. Kim, B. J. Backes, J. A. Ellman, J. Am. Chem. Soc. 1998, 720, 8011-8019.
45. The asymmetric oxidation of tBu-S-Me gave also poor results (< 25 % ee, measured by optical rotation).
46. For a general review on kinetic resolution: H. B. Kagan, J.-C. Fiaud, Top. Stereochem. 1988, 18, 249-330.
47. It was previously demonstrated that in the absence of any additive, the oxidation of sulfoxide to sulfone occurred in a non-enantioselective manner (see ref. [8]).
48. For a definition of the stereoselectivity factor s, see ref. [16].
49. For examples of asymmetric oxidations of sulfides followed by kinetic resolutions in the subsequent transformations of the sulfoxides into the sulfones, see ref. [4a].
50. For comprehensive reviews on NLE in asymmetric catalysis, see: a) C. Bolm in Advanced Asymmetric Catalysis (Ed.: G. R. Stephenson), Chapman and Hall, London, 1996, pp. 9-26;
51. b) M. Avalos, R. Babiano, P. Cintas, J. L. Jimenez, J. C. Palacios, Tetrahedron: Asymmetry 1997, 8, 2997-3017;
52. c) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
53. c) C. Girard, H. B. Kagan, Angew. Chem. 1998, 110, 3088-3127; Angew. Chem. Int. Ed. 1998, 37, 2922-2959;
54. d) D. R. Fenwick, H. B. Kagan, Top. Stereochem. 1999, 22, 257-296;
55. e) H. B. Kagan, Synlett 2001, 888-899.
56. For a review on models for non-heme carboxylate-bridged diiron metalloproteins, see: E. Y. Tshuva, S. J. Lippard, Chem. Rev. 2004, 704, 987-1012.
57. For reviews on non-heme iron catalysts in oxidation, see: a) M. Fontecave, S. Ménage, C. Duboc-Toia, Coord. Chem. Rev. 1998, 178-180, 1555-1572;
58. b) M. Costas, K. Chen, L. Que Jr., Coord. Chem. Rev. 2080, 200-202, 517-544.
59. For a recent mechanistic study on iron-catalyzed epoxidations with combinations of acetic acid and hydrogen peroxide, see: M. Fujita, L. Que Jr., Adv. Synth. Catal. 2004, 346, 190-194.
60. The ee values given in the experimental section were determined on the isolated product after chromatography on silica gel. All the fractions containing sulfoxide were mixed before the ee measurement. See: P. Diter, S. Taudien, O. Samuel, H. B. Kagan, J. Org. Chem. 1994, 59, 370-373.
61. a) K. S. Ravikumar, J.-P. Bégué, D. Bonnet-Delpon, Tetrahedron Lett. 1998, 39, 3141-3144;
62. b) K. S. Ravikumar, V. Kesavan, B. Crousse, D. Bonnet-Delpon, J.-P. Bégué, Org. Synth. Coll. Vol. 80, Wiley, New York, 2003, pp. 184-186.
63. M. J. McKennon, A. I. Meyers, J. Org. Chem. 1993, 55, 3568-3571.
64. P. Pitchen, E. Duñach, M. N. Desmukh, H. B. Kagan, J. Am. Chem. Soc. 1984, 706, 8188-8193.
65. M. Akazome, Y. Ueno, H. Ooiso, K. Ogura, J. Org. Chem. 2000, 65, 68-76.
66. G. Glahsl, R. Herrmann, J. Chem. Soc. Perkin Trans. 1 1998, 1753-1757.
67. J.-M. Brunel, P. Diter, M. Duetsch, H. B. Kagan, J. Org. Chem. 1995, 60, 8086-8088.
68. J.-M. Brunel, H. B. Kagan, Bull. Soc. Chim. Fr. 1996, 133, 1109-1115.
69. J. L. Garcĩa Ruano, C. Alemparte, M. T. Aranda, M. M. Zarzuelo, Org. Lett. 2003, 5, 75-78.