Highly enantioselective catalytic oxidation of alkyl aryl sulfides using Mn-salen catalyst

Tetrahedron

Volumn 52, Issue 44, 1996, Pages 13895-13900

  Kokubo, Chiho ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030605046     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00851-4     Document Type: Article

References (31)

1. 1. a) Barbachyn, J. D.; Johnson, C. R. In Asymmetric Synthesis; Morrison, J. D.; Scott, J. W. Eds; Academic Press: New York, 1983; Vol 4, pp227-261.
2. b) Posner, G. H. In Asymmetric Synthesis, ed by Morrison, J. D. Ed.; Academic Press: New York, 1983; Vol. 2, Chapter, 8, pp225-241.
3. c) Pitchen, P. Chem. Ind. 1994, 15 Aug, p636-639.
4. 2. Kagan, H. B. In Catalytic Asymmetric Synthesis, ed by Ojima, I. VCH, New York, 1993, pp203-226.
5. 3. a) Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086-8088.
6. b) Pitchen, P. Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188-8193.
7. c) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-299.
8. 4. Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428-1437.
9. 5. a) Nakajima, K.; Kojima, K.; Fujita, J. Chem. Lett. 1986, 1483-1486.
10. b) Colombo, A.; Matsurano, G.; Passini, A. Gazz. Chim. Ital. 1986, 116, 35-40.
11. c) Colonna, S.; Manfredi, A.; Spadoni, M.; Casella, L.; Gulotti, M. J. Chem. Soc., Perkin Trans. 1 1987, 71-73.
12. d) Sasaki, C.; Nakajima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1991, 64, 1318-1324.
13. e) Palucki, M.; Hanson, P.; Jacobsen, E. N. Tetrahedron Lett. 1992, 33, 7111-7114.
14. f) Ando, W.; Tajima, R.; Takata, T. Tetrahedron Lett. 1982, 23, 1685-1688.
15. g) Groves, J. T.; Viski, P. J. Org. Chem. 1990, 55, 3628-3634.
16. h) Naruta, Y.; Tani, F.; Maruyama, K. Tetrahedron: Asymmetry 1991, 2, 533-542.
17. i) Halterman, R. L.; Jan, S.-T.; Nimmons, H. L. Synlett 1991, 791-792.
18. j) Bolm, C.; Bienewald, F. Angew. Chem. Int. Ed. Eng. 1995, 34, 2640-2642.
19. k) Page, P. C. B.; Heer, J. P.; Collington, E. W.; Andrews, D. M. Synlett 1995, 773-775.
20. 6. a) Komatsu, N.; Nishibayashi, Y.; Sugita, T.; Uemura, S. Tetrahedron Lett. 1992, 33, 5391-5394.
21. b) Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529-4533.
22. 7. Brunel, J. M.; Kagan, H. B. Synlett 1996, 404-406.
23. 8. Alkyl hydroperoxides oxidize sulfides without catalyst. Fujita et al. have reported that this uncatalyzed reaction makes highly catalytic asymmetric oxidation of sulfides with Ti-salen complex difficult (reference 5d).
24. 9. For the recent review of Mn-salen catalyzed epoxidation, see: a) Katsuki, T. J. Synth. Org. Chem., Jpn. 1995, 53, 940-951.
25. b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214.
26. 10. a) Noda, K.; Hosoya, N.; Yanai, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1994, 35, 1887-1890.
27. b) Noda, K.; Hosoya, Irie, R.; Yamashita, Y.; Katsuki, T. Tetrahedron 1994, 50, 9609-9618.
28. 11. Although the axial chiralities of the salicyl aldehyde moieties of complexes 3 and 4 are identical, their nomenclatures are opposite to each other due to the sequence rule of IUPAC nomenclature.
29. 12. Hamada, T.; Fukuda, T.; Imanishi, H.; Katsuki, T. Tetrahedron 1996, 52, 515-530.
30. 13. Irie, R.; Ito, Y.; Katsuki, T. Synlett 1991, 265-266.
31. D +130.3° reported by us for (S)-methyl phenyl sulfoxide of 63% ee seems too large (reference 10b). Thus we correct the specific rotation of (S)-methyl phenyl sulfoxide as described in this text.