Asymmetric sulfide oxidation with vanadium catalysts and H2O2

Angewandte Chemie (International Edition in English)

Volumn 34, Issue 23, 1996, Pages 2640-2642

  Bolm, Carsten ^a   Bienewald, Frank ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Asymmetric synthesis; Catalysis; Oxidations; Sulfoxides; Vanadium compounds

Indexed keywords

EID: 33748746732     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Asymmetric catalysis in industry: a) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, Wiley, New York, 1992; b) Chirality in Industry (Eds.: A. M. Collins, G. N. Shedrake, J. Crosby), Wiley, Chichester, 1992; c) S. Kotha, Tetrahedron 1994, 50, 3639-3662; d) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, Weinheim, 1993.
2. Asymmetric catalysis in industry: a) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, Wiley, New York, 1992; b) Chirality in Industry (Eds.: A. M. Collins, G. N. Shedrake, J. Crosby), Wiley, Chichester, 1992; c) S. Kotha, Tetrahedron 1994, 50, 3639-3662; d) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, Weinheim, 1993.
3. Asymmetric catalysis in industry: a) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, Wiley, New York, 1992; b) Chirality in Industry (Eds.: A. M. Collins, G. N. Shedrake, J. Crosby), Wiley, Chichester, 1992; c) S. Kotha, Tetrahedron 1994, 50, 3639-3662; d) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, Weinheim, 1993.
4. Asymmetric catalysis in industry: a) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, Wiley, New York, 1992; b) Chirality in Industry (Eds.: A. M. Collins, G. N. Shedrake, J. Crosby), Wiley, Chichester, 1992; c) S. Kotha, Tetrahedron 1994, 50, 3639-3662; d) Catalytic Asymmetric Synthesis (Ed.: I. Ojima), VCH, New York, Weinheim, 1993.
5. For positive examples of metal-catalyzed asymmetric oxidations: a) R. A. Johnson, K. B. Sharpless in ref. [1d], pp. 227-272; b) H. C. Kolb, M. S. van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) E. N. Jacobsen in ref. [1d], pp. 159-202.
6. For positive examples of metal-catalyzed asymmetric oxidations: a) R. A. Johnson, K. B. Sharpless in ref. [1d], pp. 227-272; b) H. C. Kolb, M. S. van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) E. N. Jacobsen in ref. [1d], pp. 159-202.
7. For positive examples of metal-catalyzed asymmetric oxidations: a) R. A. Johnson, K. B. Sharpless in ref. [1d], pp. 227-272; b) H. C. Kolb, M. S. van Nieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c) E. N. Jacobsen in ref. [1d], pp. 159-202.
8. For excellent reviews see a) H. B. Kagan in ref. [1d]. S. 203-226; b) H. B. Kagan, F. Rebière, Synlett 1990, 643-650.
9. For excellent reviews see a) H. B. Kagan in ref. [1d]. S. 203-226; b) H. B. Kagan, F. Rebière, Synlett 1990, 643-650.
10. a) K. Nakajima, K. Kojima, J. Fujita, Chem. Lett. 1986, 1483-1486;
11. b) K. Nakajima, K. Kojima, M. Kojima, T. Aoyama, J. Fujita, Bull. Chem. Soc. Jpn. 1990, 63, 2620-2630.
12. Other chiral metal/Schiff base catalysts for the asymmetric sulfur oxidation: a) [Ti]: C. Sasaki, K. Nakajima, M. Kojima, J. Fujita, Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324; b) [Ti]: S. Colonna, A. Manfredi, M. Spadoni, L. Casella, M. Gullotti, J. Chem Soc. Perkin Trans 1, 1987, 71-73; c) [Ti]: A. Colombo, G. Marturano, A. Pasini, Gazz. Chim. Ital. 1986, 116, 35-40; d) [Mn]: M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett. 1992, 33, 7111-7114; e) [Mn]: K. Noda, N. Hosoay, R. Irie, Y. Yamashita, T. Katsuki, Tetrahedron 1994, 50, 9609-9618.
13. Other chiral metal/Schiff base catalysts for the asymmetric sulfur oxidation: a) [Ti]: C. Sasaki, K. Nakajima, M. Kojima, J. Fujita, Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324; b) [Ti]: S. Colonna, A. Manfredi, M. Spadoni, L. Casella, M. Gullotti, J. Chem Soc. Perkin Trans 1, 1987, 71-73; c) [Ti]: A. Colombo, G. Marturano, A. Pasini, Gazz. Chim. Ital. 1986, 116, 35-40; d) [Mn]: M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett. 1992, 33, 7111-7114; e) [Mn]: K. Noda, N. Hosoay, R. Irie, Y. Yamashita, T. Katsuki, Tetrahedron 1994, 50, 9609-9618.
14. Other chiral metal/Schiff base catalysts for the asymmetric sulfur oxidation: a) [Ti]: C. Sasaki, K. Nakajima, M. Kojima, J. Fujita, Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324; b) [Ti]: S. Colonna, A. Manfredi, M. Spadoni, L. Casella, M. Gullotti, J. Chem Soc. Perkin Trans 1, 1987, 71-73; c) [Ti]: A. Colombo, G. Marturano, A. Pasini, Gazz. Chim. Ital. 1986, 116, 35-40; d) [Mn]: M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett. 1992, 33, 7111-7114; e) [Mn]: K. Noda, N. Hosoay, R. Irie, Y. Yamashita, T. Katsuki, Tetrahedron 1994, 50, 9609-9618.
15. Other chiral metal/Schiff base catalysts for the asymmetric sulfur oxidation: a) [Ti]: C. Sasaki, K. Nakajima, M. Kojima, J. Fujita, Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324; b) [Ti]: S. Colonna, A. Manfredi, M. Spadoni, L. Casella, M. Gullotti, J. Chem Soc. Perkin Trans 1, 1987, 71-73; c) [Ti]: A. Colombo, G. Marturano, A. Pasini, Gazz. Chim. Ital. 1986, 116, 35-40; d) [Mn]: M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett. 1992, 33, 7111-7114; e) [Mn]: K. Noda, N. Hosoay, R. Irie, Y. Yamashita, T. Katsuki, Tetrahedron 1994, 50, 9609-9618.
16. Other chiral metal/Schiff base catalysts for the asymmetric sulfur oxidation: a) [Ti]: C. Sasaki, K. Nakajima, M. Kojima, J. Fujita, Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324; b) [Ti]: S. Colonna, A. Manfredi, M. Spadoni, L. Casella, M. Gullotti, J. Chem Soc. Perkin Trans 1, 1987, 71-73; c) [Ti]: A. Colombo, G. Marturano, A. Pasini, Gazz. Chim. Ital. 1986, 116, 35-40; d) [Mn]: M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett. 1992, 33, 7111-7114; e) [Mn]: K. Noda, N. Hosoay, R. Irie, Y. Yamashita, T. Katsuki, Tetrahedron 1994, 50, 9609-9618.
17. The results of mechanistic studies indicate that the catalytic reaction proceeds through the intermediacy of highly oxidized vanadium species [4]. See also R. Curci, F. Di Furia, R. Testi, G. Modena, J. Chem. Soc. Perkin Trans 2 1974, 752-757.
18. a) P. Pitchen, E. Duñach, M. N. Deshmukh, H. B. Kagan, J. Am. Chem. Soc. 1984, 106, 8188-8193;
19. b) S.-H. Zhao, O. Samuel, H. B. Kagan, Tetrahedron 1987, 43, 5135-5144;
20. c) H. B. Kagan, E. Duñach, C. Nemecek, P. Pitchen, O. Samuel, S.-H. Zhao, Pure Appl. Chem. 1985, 57, 1911-1916;
21. d) S.-H. Zhao, O. Samuel, H. B. Kagan, Org. Synth. 1989, 68, 49-54;
22. e) F. Di Furia, G. Modena, R. Seraglia, Synthesis 1984, 325-326.
23. For applications of these ligands in other metal-catalyzed reactions, see a) [Cu]: T. Aratani, Pure Appl. Chem. 1985, 57, 1839-1844; b) [Ti]: M. Hayashi, Y. Miyamoto, T. Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; c) [Ti]: M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398.
24. For applications of these ligands in other metal-catalyzed reactions, see a) [Cu]: T. Aratani, Pure Appl. Chem. 1985, 57, 1839-1844; b) [Ti]: M. Hayashi, Y. Miyamoto, T. Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; c) [Ti]: M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398.
25. For applications of these ligands in other metal-catalyzed reactions, see a) [Cu]: T. Aratani, Pure Appl. Chem. 1985, 57, 1839-1844; b) [Ti]: M. Hayashi, Y. Miyamoto, T. Inoue, N. Oguni, J. Org. Chem. 1993, 58, 1515-1522; c) [Ti]: M. Hayashi, T. Inoue, Y. Miyamoto, N. Oguni, Tetrahedron 1994, 50, 4385-4398.
26. Vanadium catalysts with structurally similar N-salicylidene amino acid ligands afford racemic sulfoxides [5b] or products with low ee values (4-14% ee); K. Nakajima, M. Kojima, K. Toriumi, K. Saito, J. Fujita, Bull. Chem. Soc. Jpn. 1989, 62, 760-767.
27. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
28. D. J. Berrisford, C. Bolm, K. B. Sharpless, Angew. Chem. 1995, 107, 1159-1171; Angew. Chem. Int. Ed. Engl. 1995, 34, 1059-1070.
29. 2 was determined to be 100:1.7 [6].
30. This behavior can be used to obtain sulfoxides with high ee values: a) N. Komatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529-4533; b) ibid. 1993, 58, 7624-7626.
31. This behavior can be used to obtain sulfoxides with high ee values: a) N. Komatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem. 1993, 58, 4529-4533; b) ibid. 1993, 58, 7624-7626.
32. The difference in reactivity between the sulfide and the sulfoxide can be used to characterize the electronic nature of the oxygen transfer reagent: W. Adam, W. Haas, B. B. Lohray, J. Am. Chem. Soc. 1991, 113, 6202-6208.
33. a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69;
34. a) R. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34-55; Angew. Chem. Int. Ed. Engl. 1991, 30, 49-69;
35. b) D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, H. B. Kagan, J. Am. Chem. Soc. 1994, 116, 9430-9439;
36. c) C. Bolm in Advanced Asymmetric Synthesis (Ed.: G. R. Stephenson), Blackie, Glasgow, in press.
37. 5 and the ligand is apparently very slow under the given reaction conditions.
38. An asymmetric vanadium(IV)-catalyzed cycloaddition: A. Togni, G. Rist, G. Rihs, A. Schweiger, J. Am. Chem. Soc. 1993, 115, 1908-1915.
39. Reviews on ligand design for oxidation catalysts: T. J. Collins, Acc. Chem. Res. 1994, 27, 279-285.
40. Peroxo vanadium complexes: A. Butler, M. J. Clague, G. E. Meister, Chem. Rev. 1994, 94, 625-638.