Synthesis of Thiiranes by Direct Sulfur Transfer: The Challenge of Developing Effective Sulfur Donors and Metal Catalysts

Chemical Reviews

Volumn 104, Issue 1, 2004, Pages 251-261

  Adam, Waldemar ^a   Bargon, Rainer M ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ETHERS; MATHEMATICAL MODELS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; OXIDATION; PHOTOLYSIS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TOXIC MATERIALS; TRANSITION METALS;

CHEMOSELECTIVITY; DIASTEREOSELECTIVITY;

SULFUR COMPOUNDS;

EID: 0942266553     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr030005p     Document Type: Review

References (121)

1. Staudinger, H.; Pfenninger, E. Ber. Dtsch. Chem. Ges. 1916, 49, 1941-1951.
2. Tabele, D. S.; Harnish, D. P. Chem. Rev. 1951, 49, 1-90.
3. Tendeloo, H. J. C. U.S. Patent 2,225,573, 1940; Chem. Abstr. 1941, 35, 2269.
4. Tendeloo, H. J. C. U.S. Patent 2,225,573, 1940; Chem. Abstr. 1941, 35, 2269.
5. Mackinney, H. W. U.S. Patent 2,962,457, 1960; Chem. Abstr. 1961, 55, 6009.
6. Mackinney, H. W. U.S. Patent 2,962,457, 1960; Chem. Abstr. 1961, 55, 6009.
7. Kaufmann, H. P.; Schickel, R. Fette, Seifen, Anstrichmittel 1983, 65, 625-639.
8. (a) Schirmeister, T. Bioorg. Med. Chem. Lett. 2000, 10, 2647-2651
9. (b) Calvo-Flores, F. G.; García-Mendoza, P.; Hernandez-Mateo, F.; Isac-García, J.; Santoyo-Gonzáles, F. J. Org. Chem. 1997, 62, 3944-3961.
10. (c) Muyake, Y. Chem. Abstr. 1980, 93, 61.
11. (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 641-667.
12. (b) Harring, S. R.; Livinghouse, T. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 1A, pp 241-250.
13. (c) Ando, W.; Choi, N. In Comprehensive Heterocydic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 1A, pp 173-240.
14. (d) Capozzi, G.; Menichetti, S.; Nativi, C. In The Synthesis of Sulphones, Sulphoxidea and Cyclic Sulphides; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1994; pp 529-641.
15. (e) Fokin, A. V.; Allakhverdiev, M. A.; Kolomiets, A. F. Russ. Chem. Rev. 1990, 59, 705-737.
16. (f) Meier, H. In Houben-Weyl, Methoden der Organischen Chemie; Klamann, D., Ed.; Thieme: Stuttgart, 1985; Vol. 11, pp 1482-1510.
17. (g) Hart, H. In Comprehensive Heterocydic Chemistry; Lwowski, E. D., Ed. ; Pergamon: Oxford, 1984; Vol. 7, pp 185-193.
18. (h) Dittmer, D. C. In Comprehensive Heterocydic Chemistry; Lwowski, E. D., Ed.; Pergamon: Oxford, 1984; Vol. 7, pp 131-184.
19. (a) Goodman, L.; Baker, B. R. J. Am. Chem. Soc. 1959, 81,4924-4926.
20. (b) van Tamelen, E. E. J. Am. Chem. Soc. 1951, 73, 3444-3448.
21. Sander, M. Chem. Rev. 1966, 66, 297-339.
22. (a) Kazemi, F.; Kiasat, A. R.; Ebrahimi, S. Synth. Commun. 2008, 33, 595-600.
23. (b) Mohammadpoor-Baltork, I.; Khosropour, A. R. Molecules 2001, 6, 996-1000; http://www.mdpi.org/molecules/papers/61200996.pdf.
24. (c) Mohammadpoor-Baltork, I.; Aliyan, H. J. Chem. Res., Synop. 2000, 3, 122-123.
25. (d) Iranpoor, N.; Adibi, H. Bull. Chem. Soc. Jpn. 2000, 73, 675-680.
26. (e) Tangestinejad, S.; Mirkhani, V. J. Chem. Res. 1999, 6, 370-371.
27. (f) Iranpoor, N.; Jeynizadeh, B. Synth. Commun. 1998, 28, 3913-3918.
28. (g) Mohammad-Baltork, I.; Aliyan, H. Synth. Commun. 1998, 28, 3943-3949.
29. (a) Strauaz, O. P. Adv. Chem. Ser. 1972, 110, 137-149
30. (b) Gunning, H. E.; Strausz, O. P. Adv. Photochem. 1966, 4, 143-194.
31. Hawkins, M.; Almond, M. J.; Downs, A. J. J. Phys. Chem. 1985, 89, 3326-3334.
32. Sidhu, K. S.; Lown, E. M.; Strausz, O. P.; Gunning, H. E. J. Am. Chem. Soc. 1966, 88, 254-263.
33. (a) Lown, E. M.; Dedio, E. L.; Strausz, O. P.; Gunning, H. E. J. Am. Chem. Soc. 1967, 89, 1056-1062.
34. (b) Knight, A. R.; Strausz, O. P.; Gunning, H. E. J. Am. Chem. Soc. 1963, 85, 2349-2355.
35. Little, D. J.; Dalgleish, A.; Donovan, R. J. Faraday Discuss. Chem. Soc. 1972, 53, 211-216.
36. (a) Davies, D. D.; Klemm, R. B. Int. J. Chem. Kinet. 1973, 5, 841-857
37. (b) Davies, D. D.; Klemm, R. B. Braun, W.; Pilling, M. Int. J. Chem. Kinet. 1972, 4, 383-394.
38. (c) Strausz, O. P.; O'Callaghan, W. B.; Lown, E. M.; Gunning, H. E. J. Am. Chem. Soc. 1971, 93, 559-560.
39. (d) Donovan, R. J.; Husain, D.; Fair, R. W.; Strausz, O. P.; Gunning, H. E. Trans. Faraday Soc. 1970, 66, 1635-1641.
40. (a) Sherwood, A. G.; Safarik, I.; Verkoczy, B.; Almadi, G.; Wiebe, H. A. ; Strausz, O. P. J. Am. Chem. Soc. 1979, 101, 3000-3004.
41. (b) Lown, E. M.; Dedio, E. L.; Strausz, O. P.; Gunning, H. E. J. Am. Chem. Soc. 1967, 89, 1056-1062.
42. Leppin, E.; Gollnick, K. Tetrahedron Lett. 1969, 43, 3819-3824.
43. Joseph, J.; Gosavi, R. K.; Otter, A.; Kotovych, G.; Lown, E. M.; Strausz, O. P. J. Am. Chem. Soc. 1990, 112, 8670-8678.
44. Green, Verkoczy, B.; Lown, E. M.; Strausz, O. P. J. Am. Chem. Soc. 1985, 63, 667-675.
45. Leppin, E.; Gollnick, K. J. Am. Chem. Soc. 1971, 93, 2848-2853.
46. Okazaki, R.; Okawa, K.; Weijiki, S. Inamoto, N. Bull. Chem. Soc. Jpn. 1971, 44, 3167-3170.
47. Bertaïna, C.; Fellous, R.; Lemaire, F.; Stringat, R. Tetrahedron Lett. 1985, 26, 5521-5522.
48. Leppin, E.; Gollnick, K. Chem. Ber. 1970, 103, 2894-2901.
49. (a) Nau, W.; Bucher, G.; Scaiano, J. C. J. Am. Chem. Soc. 1997, 119, 1961-1970.
50. (b) Peppard, T. L.; Sharpe, F. R. J. Chem. Soc., Perkin Trans. 1 1980, 311-313.
51. (c) Jahn, R.; Schmidt, U. Monatsh. Chem. 1978, 109, 161-164.
52. (d) Schmidt, U.; Kabitze, K.; Boie, I.; Osterroht, C. Chem. Ber. 1988, 98, 3819-3826.
53. Leppin, E.; Gollnick, K. Chem. Ber. 1970, 103, 2571-2580.
54. Sugihara, Y.; Noda, K.; Nakayama, J. Tetrahedron Lett. 2000, 41, 8913-8916.
55. Ashitani, T.; Nagahama, S. Nat. Prod. Lett. 1999, 13, 163-167.
56. Nakayama, J.; Ito, Y.; Mizumura, A. Sulfur Lett. 1992, 14, 247-250.
57. Bartlett, P. D.; Ghosh, T. J. Org. Chem. 1987, 52, 4937-4943.
58. Emsley, J.; Griffiths, D. W.; Jayne, G. J. J. J. Chem. Soc., Perkin Trans. 1 1979, 228-232.
59. Inoue, S.; Tezuka, T.; Oae, S. Phosphorus Sulfur 1978, 4, 219-221.
60. Ando, W.; Sonobe, H.; Akasaka, T. Tetrahedron 1990, 46, 5093-5100.
61. (a) Luccini, V.; Modena, G.; Pasquato, L. Gozz. Chim. Ital. 1997, 127, 177-188.
62. (b) Capozzi, G.; Modena, G.; Pasquato, L. The Chemistry of Sulphenyl Halides and Sulphenamides; Patai, S., Ed.; Wiley: Chichester, U.K., 1990; pp 403-516.
63. Fachini, M.; Lucchini, V.; Modena, G.; Pasi, M.; Pasquato, L. J. Am. Chem. Soc. 1999, 121, 1, 3944-3950.
64. Pasquato, L. Speciality Chem. Mag. 2002, 22, 21-22, 24.
65. Boster, J.; Kellogg, R. M. J. Chem. Soc. Chem. Commun. 1978, 630-631.
66. (a) Abu-Yousef, I. A.; Harpp, D. N. J. Org. Chem. 1997, 62, 8366-8371.
67. (b) Abu-Yousef, I. A.; Harpp, D. N. Tetrahedron Lett. 1995, 36, 201-204.
68. Abu-Yousef, I. A.; Hynes, R. C.; Harpp, D. N. Tetrahedron Lett. 1993, 34, 4289-4292.
69. Kowalski, J.; Chojnowski, J.; Michalski, J. J. Organomet. Chem. 1983, 258, 1-5.
70. Capozzi, F.; Capozzi, G.; Menichetti, S. Tetrahedron Lett. 1988, 29, 4177-4180.
71. (a) Tolstikov, G. A.; Lerman, B. M.; Belogaeva, T. A. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Trans.) 1986, 35, 563-566.
72. (b) Tolstikov, G. A.; Lerman, B. M.; Umanskaya, L. I.; Struchkov, Y. T. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Trans.) 1982, 31, 588-595.
73. (c) Tolstikov, G. A.; Lerman, B. M.; Umanskaya, L. I.; Struchkov, Y. T.; Espenbetov, A. A.; Yanovsky, A. L. Tetrahedron Lett. 1980, 21, 4189-4192.
74. Tolstikov, G. A.; Lerman, B. M.; Belogaeva, T. A. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Trans.) 1988, 37, 1629-1635.
75. Matturro, M. G.; Reynolds, R. P.; Kastrup, R. V.; Pictroski, C. F. J. Am. Chem. Soc. 1986, 108, 8, 2775-2776.
76. Adam, W.; Weinkötz, S. J. Chem. Soc. Chem. Commun. 1996, 177-178.
77. Adam, W.; Fröhling, B.; Peters, K.; Weinkötz, S. J. Am. Chem. Soc. 1998, 120, 8914-8919.
78. Shea, K. J.; Kim, J.-S. J. Am. Chem. Soc. 1992, 114, 3044-3051.
79. Zipplies, M. F.; de Vos, M. J.; Bruice, T. C. J. Org. Chem. 1985, 50, 3228-3230.
80. Adam, W.; Deeg, O.; Weinkötz, S. J. Org. Chem. 1997, 62, 7084-7085.
81. (a) Snyder, J. P. J. Am. Chem. Soc. 1974, 96, 5005-5007.
82. (b) Carlsen, L.; Harrit, A.; Holm, A. J. Chem. Soc., Perkin Trans. 1 1976, 1404-1407.
83. (c) Carlsen, L.; Snyder, J. P.; Holm, A.; Pedersen, E. Tetrahedron 1981, 37, 1257-1261.
84. (d) Karlström, G.; Roos, B. O.; Carlsen, L. J. Am. Chem. Soc. 1984, 106, 1557-1561.
85. Adam, W.; Fröhling, B. Org. Lett. 2000, 16, 2519-2522.
86. Adam, W.; Bosio, S. G.; Fröhling, B.; Leusser, D.; Stalke, D. J. Am. Chem. Soc. 2002, 124, 8316-8820.
87. Huisgen, R.; Mloston, G.; Polborn, K.; Palacios-Gambra, F. Liebigs Ann./Recl. 1997, 187-192.
88. Adam, W.; Weinkötz, S. J. Am. Chem. Soc. 1998, 120, 4861-4862.
89. Baudin, J.-B.; Commenil, M.-G.; Julia, S. A.; Wang, Y. Bull. Soc. Chim. Fr. 1996, 133, 515-529.
90. Adam, W.; Fröhling, B. Org. Lett. 2002, 4, 599-602.
91. Fröhling, B. Dissertation, University of Würzburg, 2002.
92. Adam, W.; Fröhling, B. J. Org. Chem. 1998, 63, 9154-9155.
93. Adam, W.; Bargon, R. M.; Mloston, G. Eur. J. Org. Chem. 2003, 4012-4015.
94. (a) Wentrup, C.; Kambouris, P. Chem. Rev. 1991, 97, 363-373.
95. (b) Wentrup, C.; Flamang, R. J. Phys. Org. Chem. 1998, 11, 350-355.
96. Adam, W.; Bargon, R. M. Eur. J. Org. Chem. 2001, 1959-1962.
97. Adam, W.; Curci, R.; D'Accolti, L.; Dinoi, C.; Fusoo, C.; Gasparrini, F. ; Kluge, R.; Paredes, R.; Schulz, M.; Smerz, A. K.; Veloza, L. A.; Weinkötz, S.; Winde, R. Chem. Eur. J. 1997, 3, 105-109.
98. Yu, Z.-X.; Wu, Y.-D. J. Org. Chem. 2003, 68, 6049-6052.
99. Taqui Khan, M. M.; Siddiqui, M. R. H. Inorg. Chem. 1991, 30, 1157-1159.
100. Kendall, J. D.; Simpkins, N. S. Synlett 1998, 391-392.
101. Yan, W. F.; Young, C. G. Aust. J. Chem. 1991, 44, 361-367.
102. Chen, G. J.-J.; McDonald, J. W.; Newton, W. E. Inorg. Chem. 1976, 15, 2612-2615.
103. Young, C. G. J. Chem. Educ. 1995, 72, 751-753.
104. Schultz, F. A.; Ott, V. R.; Rolison, D. S.; Bravard, D. C.; McDonald, J. W.; Newton, W. E. Inorg. Chem. 1978, 17, 1758-1765.
105. Adam, W.; Bargon, R. M.; Schenk, W. A. J. Am. Chem. Soc. 2003, 125, 3871-3876.
106. Adam, W.; Bargon, R. M. Chem. Commun. 2001, 1910-1911.
107. Adam, W.; Bargon, R. M.; Bosio, S. G., Schenk, W. A.; Stalke, D. J. Org. Chem. 2002, 67, 7037-7041.
108. (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
109. (b) Erden, I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 1A, pp 97-171.
110. (c) Katsuki, T. In Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N., Pfaltz, A.; Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. 2, pp 621-648.
111. (d) Johnson, R. A.; Sharpless, K. B. Catalytic Asymmetric Synthesis; 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; pp 231-280.
112. (e) Dusi, M.; Mallat, T.; Baiker, A. Catal. Rev. 2000, 42, 213-278.
113. (f) Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Bull. Soc. Chim. Fr. 1995, 132, 769-800.
114. (g) Wang, Z. X.; Tu, Y.; Frohn, M.; Zhang, J. R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 9, 11224-11235.
115. (h) Denmark, S. E.; Wu, Z. C.; Crudden, C. M.; Matsuhashi, H. J. Org. Chem. 1997, 62, 8288-8289.
116. (a) Huisgen, R. Phosphorus Sulfur 1989, 43, 63-94.
117. (b) Chew, W.; Hynes, R. C.; Harpp, D. N. J. Org. Chem. 1993, 58, 4398-4404.
118. (c) Chew, W.; Harpp, D. N. J. Org. Chem. 1993, 58, 8, 4405-4410.
119. (d) Steudel, R. Chem. Eur. J. 2002, 8, 217-228.
120. (a) Halpern, J. Pure Appl. Chem. 1989, 20, 59-75.
121. (b) Adam, W.; Korb, M. N.; Roschmann, K. J.; Saha-Möller, C. R. J. Org. Chem. 1998, 63, 3423-3428.