Oxidation of Thioether Ligands in Pseudotetrahedral Cyclopentadienylruthenium Complexes: Toward a New Stereoselective Synthesis of Chiral Sulfoxides

Inorganic Chemistry

Volumn 36, Issue 11, 1997, Pages 2372-2378

  Schenk, Wolfdieter A ^a   Frisch, Jürgen ^a   Dürr, Michael ^a   Burzlaff, Nicolai ^a   Stalke, Dietmar ^a   Fleischer, Roland ^a   Adam, Waldemar ^a   Prechtl, Frank ^a   Smerz, Alexander K ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001141536     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic961280f     Document Type: Article

References (66)

1. Enantioselective Organic Syntheses Using Chiral Transition Metal Complexes. 2. Part 1: Schenk, W. A.; Frisch, J.; Adam, W.; Prechtl, F. Angew. Chem. 1994, 106, 1699; Angew. Chem., Int. Ed. Engl. 1994, 33, 1609.
2. Enantioselective Organic Syntheses Using Chiral Transition Metal Complexes. 2. Part 1: Schenk, W. A.; Frisch, J.; Adam, W.; Prechtl, F. Angew. Chem. 1994, 106, 1699; Angew. Chem., Int. Ed. Engl. 1994, 33, 1609.
3. (a) Institut für Anorganische Chemie.
4. (b) Institut für Organische Chemie.
5. (a) Posner, G. H. Acc. Chem. Res. 1987, 20, 72.
6. (b) Solladie, G. Pure Appl. Chem. 1988, 60, 1699.
7. Durst, T. In Comprehensive Organic Chemistry; Barton, D., Ollis, D., Eds.; Pergamon: Oxford, U.K., 1979; Vol. 3, p 121.
8. Kagan, H. B.; Rebiere, F.; Samuel, O. Phosphorus Sulfur Silicon 1991, 58, 89.
9. (a) Andersen, K. K.; Bujnicki, B.; Drabowicz, J.; Mikolajczyk, M.; O'Brien, J. B. J. Org. Chem. 1984, 49, 4070.
10. (b) Rebiere, F.; Samuel, O.; Richard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991.
11. Evans, D. A.; Faul, M. M.; Colombo, L.; Biaha, J. J.; Clardy, J.; Cherry, D. J. Am. Chem. Soc. 1992, 114, 5977 and references cited therein.
12. Holland, H. L. Chem. Rev. 1988, 88, 473.
13. (a) Davis, F. A.; McCauley, J. P.; Chattopadhyay, S.; Harakal, M. E.; Towson, J. C.; Watson, W. H.; Tavanaiepour, I. J. Am. Chem. Soc. 1987, 109, 3370.
14. (b) Melanidis, V.; Verfürth, U.; Herrmann, R. Z. Naturforsch., B 1990, 45, 1689.
15. Davis, F. A.; Reddy, R. T.; Han, W.; Carroll, P. J. J. Am. Chem. Soc. 1992, 114, 1428.
16. Pointner, A.; Herrmann, R. Z. Naturforsch., B 1995, 50, 1396.
17. (a) Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188.
18. (b) DiFuria, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325.
19. (a) Colonna, S.; Gaggero, N.; Manfredi, A.; Casella, L.; Gullotti, M. J. Chem. Soc., Chem. Commun. 1988, 1451.
20. (b) Colonna, S.; Gaggero, N. Tetrahedron Lett. 1989, 30, 6233.
21. Colonna, S.; Gaggero, N. Phosphorus Sulfur Silicon 1994, 95-96, 103.
22. (a) Madesclaire, M. Tetrahedron 1986, 42, 5459.
23. (b) Drabowicz, J. Kielbasinski, P.; Mikolajczyk, M. In The Chemistry of Sulfines and Sulfoxides; Patai, S., Rappoport, B., Stirling, C. J. M., Eds.; Wiley, New York, 1988; p 233.
24. (a) Adams, R. D.; Chodosh, D. F. J. Am. Chem. Soc. 1978, 100, 812.
25. (b) Adams, R. D.; Blankenship, C.; Segmüller, B. E.; Shiralian, M. J. Am. Chem. Soc. 1983, 105, 4319.
26. Yoshida, T.; Adochi, T.; Sato, K.; Baba, K.; Kanokogi, T. J. Chem. Soc., Chem. Commun. 1993, 1511.
27. (a) Biscarini, P.; Fusina, L.; Nivellini, G. D. J. Chem. Soc. A 1971, 1128.
28. (b) Goggin, P. L.; Goodfellow, R. J.; Reed, F. J. S. J. Chem. Soc. Dalton Trans. 1974, 576.
29. Fergusson, J. E.; Page, C. T.; Robinson, W. T. Inorg. Chem. 1976, 15, 2270.
30. (a) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205.
31. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187.
32. Adam, W.; Hadjiarapoglou, L. P.; Curci, R.; Mello, H. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; p 195.
33. Adam, W.; Smerz, A. K. Bull. Chim. Soc. Belg. 1996, 105, 581.
34. Schenk, W. A.; Frisch, J.; Adam, W.; Prechtl, F. Inorg. Chem. 1992, 31, 3329.
35. Perez-Encabo, A.; Perrio, S.; Slawin, A. M. Z.; Thomas, S. E.; Wierchleyski, A. T.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1993, 1059.
36. (a) Hewertson, W.; Watson, H. R. J. Chem. Soc. 1962, 1491.
37. (b) Butter, S. A.; Chatt, J. Inorg. Chem. 1974, 15, 185.
38. King, R. B.; Cluyd, J. C. J. Am. Chem. Soc. 1975, 97, 53.
39. (a) Bruce, M. I.; Hameister, C.; Swincer, A. G.; Wallis, R. C. Inorg. Synth. 1982, 21, 78.
40. (b) Ashby, G. S.; Bruce, M. I.; Tomkins, I. B.; Wallis, R. C. Aust. J. Chem. 1979, 32, 1003.
41. Davies, S. G.; Simpson, S. J. J. Chem. Soc., Dalton Trans. 1984, 993.
42. Consiglio, G.; Morandini, F.; Bangerter, F. Inorg. Chem. 1982, 21, 455.
43. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. P. Chem. Ber. 1991, 124, 2377.
44. (b) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2817.
45. (a) North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr. 1968, A24, 351.
46. (b) Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
47. Sheldrick, G. M. Program for crystal structure refinement. University of Göttingen, 1993.
48. Kottke, T.; Stalke, D. J. Appl. Crystallogr. 1993, 26, 615.
49. Davies, S. G.; McNally, J. P.; Smallridge, A. J. Adv. Organomet. Chim 1990, 30, 1.
50. Schenk, W. A.; Stur, T. Z. Naturforsch., B 1990, 45, 1495.
51. Abel, E. W.; Bhargava, S. K.; Orrell, K. G. Prog. Inorg. Chem. 1984, 32, 1.
52. Ohkita, K.; Kurosawa, H.; Hirao, T.; Ikeda, I. J. Organomet. Chem. 1994, 470, 179.
53. Mendez, N. Q.; Arif, A. M.; Gladysz, J. Organometallics 1991, 10, 2199.
54. Faller, J. W.; Ma, Y. Organometallics 1992, 11, 2726.
55. (a) Seeman, J. I.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1984, 1019.
56. (b) Davies, S. G.; Seeman, J. I. Tetrahedron Lett. 1984, 25, 1845.
57. Seeman, J. I. Pure Appl. Chem. 1987, 59, 1661.
58. Halpern, J. Science 1982, 217, 401 and references cited therein.
59. Orpen, A. G. Chem. Soc. Rev. 1993, 22, 191.
60. (a) Bezler, J. Dissertation, University of Würzburg, 1995.
61. (b) Schenk, W. A.; Bezler, J. Unpublished results.
62. (a) Astruc, D. Angew. Chem. 1988, 100, 662; Angew. Chem., Int. Ed. Engl. 1988, 27, 643.
63. (a) Astruc, D. Angew. Chem. 1988, 100, 662; Angew. Chem., Int. Ed. Engl. 1988, 27, 643.
64. (b) Baird, M. C. Chem. Rev. 1988, 88, 1217.
65. Schenk, W. A.; Dürr, M. To be published.
66. A reviewer suggested that in a mechanism such as described by Scheme 1 the ee's might be temperature dependent. We have found no pronounced changes in the -20 to 0°C range (at higher temperatures DMD decomposes too rapidly), but are addressing this question using other oxidants.