Catalytic asymmetric oxidation of tert-butyl disulfide. Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines

Journal of the American Chemical Society

Volumn 120, Issue 32, 1998, Pages 8011-8019

  Cogan, Derek A ^a   Liu, Guangcheng ^a,b   Kim, Kyungjin ^a,c   Backes, Bradley J ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b GLAXOSMITHKLINE   (United States)

^c HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; SULFINAMIDE; SULFOXIDE; TERT BUTANESULFINAMIDE; TERT BUTANESULFINIMINE; TERT BUTYL DISULFIDE; TERT BUTYL SULFOXIDE; TERT BUTYL TERT BUTANETHIOSULFINATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTALLIZATION; ENANTIOMER; OXIDATION; STEREOCHEMISTRY; STEREOSPECIFICITY; SULFATION;

EID: 0032547296     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9809206     Document Type: Article

References (78)

1. (a) Solladié. G. Synthesis 1981, 185-196.
2. (b) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
3. (c) Patai, S. The Chemistry of Sulphinic Acids, Esters and their Derivatives; John Wiley & Sons: Chichester, England, 1990.
4. (d) Barbachyn, M. R.; Johnson, C. R. In Asymmetric Synthesis; Morrison, J. D., Scott, J. W., Eds.; Academic Press: New York, 1983; Vol. 4, p 227.
5. Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Reddy, G. V.; Zhou, P. Phosphorus, Sulfur, Silicon Relat. Elem. 1997, 120&121, 291-303.
6. (a) Liu, G.; Cogan, D.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913-9914.
7. (b) Moreau, P.; Essiz, M.; Mérour, J.-Y.; Bouzard, D. Tetrahedron: Asymmetry 1997, 8, 591-598.
8. (c) Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans. I 1982, 341-343.
9. (d) Yang, T.-K.; Chen, R.-Y.; Lee, D.-S.; Peng, W.-S.; Jiang, Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem. 1994, 59, 914-921.
10. Review: Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13-18.
11. (a) Davis, F. A.; Zhou, P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243-3245.
12. (b) Ruano, J. L. G.; Fernández, I.; Catalina, M. d.; Cruz, A. A. Tetrahedron: Asymmetry 1996, 7, 3407-3414.
13. (c) Davis, F. A.; Zhou, P. Tetrahedron Lett. 1994, 35, 7525-7528.
14. (d) Davis, F. A.; Reddy, G. V.; Liang, C.-H. Tetrahedron Lett. 1997, 38, 5139-5142.
15. (a) Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J. Tetrahedron: Asymmetry 1997, 8, 3991-3994.
16. (b) Lefebvre, I. M.; Evans, S. A., Jr. J. Org. Chem. 1997, 62, 7532-7533.
17. (c) Mikolajczyk, M.; Lyzwa, P.; Drabowicz, J.; Wieczorek, M. W.; Blaszczyk, J. J. Chem. Soc., Chem. Commun. 1996, 1503-1504.
18. (a) Andersen, K. K. In The Chemistry of Sulfones and Sulfoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; John Wiley & Sons: New York, 1988; Chapter 3, pp 56-94.
19. (b) Kagan, H. B.; Rebiere, F. SYNLETT 1990, 643-649.
20. (c) Solladié, G. Synthesis 1981, 185-196.
21. Casey, M.; Manage, A. C.; Gairns, R. S. Tetrahedron Lett. 1989, 30, 6919-6922.
22. Durst, T.; Viau, R.; McClory, M. R. J. Am. Chem. Soc. 1971, 93, 3077-3078.
23. For examples of enolate alkylation and derivatizable cleavage from solid support, see: (a) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172. (b) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056.
24. For examples of enolate alkylation and derivatizable cleavage from solid support, see: (a) Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171-11172. (b) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3055-3056.
25. Backes, B. J.; Ellman, J. A. Abstracts of Papers, 213th National Meeting of the American Chemical Society, San Francisco, CA; American Chemical Society: Washington, DC, 1997; ORGN 066.
26. In one case, 3 has been prepared in situ and directly consumed: Bleeker, I. P.; Engberts, J. B. F. N. J. Org. Chem. 1981, 46, 1012-1014.
27. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555-2563.
28. (a) Fernández, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789-6796.
29. (b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1994, 35, 5719-5722.
30. Other sulfinamides are less optically stable: Booms, R. E.; Cram, D. J. J. Am. Chem. Soc. 1972, 94, 5438-5446
31. (a) Evans, D. A.; Faul, M. M.; Colombo, L.; Bisaha, J. J.; Clardy, J.; Cherry, D. J. Am. Chem. Soc. 1992, 114, 5977-5985.
32. (b) Rebiére, F.; Samuel, O.; Ricard, L.; Kagan, H. B. J. Org. Chem. 1991, 56, 5991-5999.
33. Netscher, T.; Prinzbach, H. Synthesis 1987, 683-688.
34. (a) Komatsu, N.; Hahizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624-7626.
35. (b) Lattanzi, A.; Bonadies, F.; Senatore, A.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2473-2478.
36. Bolm, C.; Bienewald, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 2640-2642.
37. (a) Hayashi, M.; Inoue, T.; Miyamoto, Y.; Oguni, N. Tetrahedron 1994, 50, 4385-4398.
38. (b) Hayashi, M.; Tanaka, K.; Oguni, N. Tetrahedron: Asymmetry 1995, 6, 1833-1836.
39. (c) Hayashi, M.; Kaneda, H.; Oguni, N. Tetrahedron: Asymmetry 1995, 6, 2511-2516.
40. (d) Aratani, T. Pure Appl. Chem. 1985, 57, 1839-1844.
41. (a) Sagramora, L.; Koch, P.; Garbesi, A.; Fava, A. J. Chem. Soc., Chem. Commun. 1967, 985-986.
42. (b) Mikolajcyk, M.; Drabowicz, J. J. Chem. Soc., Chem. Commun. 1976, 220-221.
43. (c) Kishi, M.; Ishihara, S.; Komeno, T. Tetrahedron 1974, 30, 2135-2142.
44. (a) Block, E.; O'Connor, J. J. Am. Chem. Soc. 1974, 96, 6, 3921-3929.
45. (b) Block, E.; O'Connor, J. J. Am. Chem. Soc. 1974, 96, 3929-3944.
46. Takata, T.; Endo, T. In The Chemistry of Sulfinic Acids, Esters and Their Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, England, 1990; pp 527-575.
47. The absolute sense of stereochemistry was assigned by addition of MeMgBr, known to proceed with inversion (vide infra), to deliver (S)-tert-butyl methyl sulfoxide.
48. (a) Savage, W. E.; Fava, A. J. Chem. Soc., Chem. Commun. 1965, 417-418.
49. (b) Kice, J. L.; Large, G. B. Tetrahedron Lett. 1965, 3537-3541.
50. Davis, F. A.; Jenkins, R. H. J.; Awad, S. B.; Stringer, O. D.; Watson, W. H. J. Am. Chem. Soc. 1982, 104, 5412-5418.
51. Nemecek, C.; Duñach, E.; Kagan, H. B. New J. Chem. 1986, 10, 761-764.
52. Drabowicz, J.; Mikolajczyk, M. Tetrahedron Lett. 1985, 26, 5703-5706.
53. Hayashi, M.; Inoue, T.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 341-342.
54. See the Experimental Section for details.
55. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070.
56. (a) Oguni, N.; Matsuda, Y.; Kaneko, T. J. Am. Chem. Soc. 1988, 110, 7877-7878.
57. (b) Kitamura, M.; Okada, S.; Noyori, R. J. Am. Chem. Soc. 1989, 111, 4028-4036.
58. Butler, A.; Clague, M. J.; Meister, G. E. Chem. Rev. 1994, 94, 625-638.
59. Hirao, T. Chem. Rev. 1997, 97, 2707-2724.
60. (a) Clague, M. J.; Keder, N. L.; Butler, A. Inorg. Chem. 1993, 32, 4754-4761.
61. (b) Rehder, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 148-167.
62. (c) Hamstra, B. J.; Colpas, G. J.; Pecoraro, V. L. Inorg. Chem. 1998, 37, 949-955 and references therein.
63. (a) Mimoun, H.; Mignard, M.; Brechot, P.; Saussine, L. J. Am. Chem. Soc. 1986, 108, 3711-3718.
64. (b) Nakajima, K.; Kojima, M.; Toriumi, K.; Saito, K.; Fujita, J. Bull. Chem. Soc. Jpn. 1989, 62, 760-767.
65. (c) Schmidt, H.; Baskirpoor, M.; Rehder, S. J. Chem. Soc., Dalton Trans. 1996, 3865-3870.
66. Page, P. C. B.; Heer, J. P.; Bethell, D.; Collington, E. W.; Andrews, D. M. SYNLETT 1995, 773-775.
67. (a) Mikolajczyk, M. Phosphorus Sulfur 1986, 27, 31-42.
68. (b) Mikolajczyk, M.; Drabowicz, J. In Topics in Stereochemistry; Allinger, N. L., Eliel, E. L., Wilen, S. H., Eds.; John Wiley & Sons: New York, 1982; Vol. 13, pp 333-468.
69. (c) Okuyama, T. In The Chemistry of Sulfinic Acids, Esters and Their Derivatives; Patai, S., Ed.; John Wiley & Sons: Chichester, England, 1990; pp 623-638.
70. Holmes, R. Acc. Chem. Res. 1979, 12, 257-265.
71. A cation effect may also be responsible. Addition of LiHMDS in DAG sulfinate esters is stereospecific, but NaHMDS proceeds with considerable racemization. Kim, K.; Backes, B. J.; Ellman, J. A., unpublished results.
72. Drabowicz, J.; Dudzinski, B.; Mikolajczyk, M.; Wieczorek, M. W.; Majzner, W. R. Tetrahedron: Asymmetry 1998, 9, 1171-1178.
73. Larrow, J. F.; Jacobsen, E. N. J. Org. Chem. 1994, 59, 1939-1942.
74. (a) Tramposch, K. M.; Kung, H. F.; Blau, M. J. Med. Chem. 1983, 26, 121-125.
75. (b) Zwanenburg, D. J.; Reynen, W. A. P. Synthesis 1976, 624-625.
76. To attain the optimal interface surface area, the crystallizing dish described here was effective. For 0.5-mol-scale oxidations of disulfide 1, a simple 500-mL Erlenmeyer flask provided the best interface area. Stirring was always performed with a magnetic stir bar; overhead mechanical stirrers break the organic-aqueous interface.
77. Bergbreiter, D. E.; Lalonde, J. J. J. Org. Chem. 1987, 52, 1601-1603.
78. Drabowicz, J.; Lyzwa, P.; Popielarczyk, M.; Mikolajczyk, M. Synthesis 1990, 937-938.