A novel and direct α-azidation of cyclic sulfides using a hypervalent iodine(III) reagent

Abstract

A novel and direct α-azidation of cyclic sulfides using a hypervalent iodine(III) reagent in the presence of Me₃SiN₃ is described; the present method is applicable to substrates which are easily aromatized under oxidative conditions.

References

1. I. W. J. Still, W. L. Brown, R. J. Colville and G. W. Kutney, Can. J. Chem., 1984, 62, 586 and references cited therein.
2. B. M. Trost and W. H. Pearson, J. Am. Chem. Soc., 1981, 103, 2483; A. Hassner, P. Munger and B. A. Belinka Jr., Tetrahedron Lett., 1982, 23, 699.
3. E. M. Suh and Y. Kishi, J. Am. Chem. Soc., 1994, 116, 11 205; J. Zaloom, M. Calandra and D. C. Roberts, J. Org. Chem., 1985, 50, 2601; J. Garcia, F. Urpi and J. Vilarrasa, Tetrahedron Lett., 1984, 25, 4841 Review: E. F. V. Scriven and K. Turnbull, Chem. Rev., 1988, 88, 297.
4. G. C. Barrett, in Comprehensive Organic Chemistry, ed. D. Barton and W. D. Ollis, Pergamon, Oxford, 1979, vol. 3, p. 55.
5. C. Z. Ding and R. B. Silverman, Synth. Commun., 1993, 23, 1467; G. Apitz and W. Steglich, Tetrahedron Lett., 1991, 32, 3163; A. R. Katritzky, M. Szajda and S. Bayyuk, Synthesis, 1986, 804; H. Sakai, K. Ito and M. Sekiya, Chem. Pharm. Bull., 1973, 21, 2257.
6. A. F. Janzen, G. N. Lypka and R. E. Wasylishen, J. Heterocycl. Chem., 1979, 16, 415; S. Rakhit, M. Georges and J. F. Bagli, Can. J. Chem., 1979, 57, 1153; U. Lerch and J. G. Moffatt, J. Org. Chem., 1971, 36, 3391.
7. H. Böhme and D. Morf, Chem. Ber., 1957, 90, 446.
8. H. Böhme and F. Ziegler, Liebigs Ann. Chem., 1974, 734.
9. B. M. Trost, M. Vaultier and M. L. Santiago, J. Am. Chem. Soc., 1980, 102, 7929.
10. N. B. Perry, J. W. Blunt and M. H. G. Munro, Tetrahedron, 1988, 44, 1727.
11. N. B. Perry, J. W. Blunt, M. H. G. Munro, T. Higa and R. Sakai, J. Org. Chem., 1988, 53, 4127; J. W. Blunt, M. H. G. Munro, C. N. Battershill, B. R. Copp, J. D. McCombs, N. B. Perry, M. R. Prinsep and A. M. Thompson, New J. Chem., 1990, 14, 761.
12. J.-F. Cheng, Y. Ohizumi, M. R. Wälchli, H. Nakamura, Y. Hirata, T. Sasaki and J. Kobayashi, J. Org. Chem., 1988, 53, 4621 and references cited therein.
13. D. C. Radisky, E. S. Radisky, L. R. Barrows, B. R. Copp, R. A. Kramer and C. M. Ireland, J. Am. Chem. Soc., 1993, 115, 1632.
14. Y. Tamura, T. Yakura, J. Haruta and Y. Kita, Tetrahedron Lett., 1985, 26, 3837; J. Org. Chem., 1987, 52, 3927; Y. Kita, H. Tohma, K. Kikuchi, M. Inagaki and T. Yakura, J. Org. Chem., 1991, 56, 435; Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka and T. Yakura, J. Am. Chem. Soc., 1992, 114, 2175; Y. Kita, R. Okunaka, M. Kondo, H. Tohma, M. Inagaki and K. Hatanaka, J. Chem. Soc., Chem. Commun., 1992, 429; Y. Kita, T. Takada, S. Mihara, B. A. Whelan and H. Tohma, J. Org. Chem., 1995, 60, 7144; Y. Kita, M. Gyoten, M. Ohtsubo, H. Tohma and T. Takada, Chem. Commun., 1996, 1481; Y. Kita, M. Egi, A. Okajima, M. Ohtsubo, T. Takada and H. Tohma, Chem. Commun., 1996, 1491; Y. Kita, M. Egi, M. Ohtsubo, T. Saiki, T. Takada and H. Tohma, Chem. Commun., 1996, 2225.
15. Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka and T. Yakura, Tetrahedron Lett., 1991, 32, 4321; Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai and S. Oka, J. Am. Chem. Soc., 1994, 116, 3684.
16. Y. Kita, H. Tohma, T. Takada, S. Mitoh, S. Fujita and M. Gyoten, Synlett, 1994, 427.
17. The reaction of 1a with PhI(OCOCF₃)₂ in MeOH gave the corresponding sulfoxide in 89% yield. For previously reported examples: see J. P. A. Castrillón and H. H. Szmant, J. Org. Chem., 1967, 32, 976; A. W. Czarnik, J. Org. Chem., 1984, 49, 924; G. F. Koser, P. B. Kokil and M. Shah, Tetrahedron Lett., 1987, 28, 5431; D. G. Ray III and G. F. Koser, J. Am. Chem. Soc., 1990, 112, 5672 and references cited therein.
18. The formation of hypervalent azido iodine(III) reagents by the reaction of Me₃SiN₃ with PhI = O at –40 °C has been reported; Magnus and Lacour, J. Am. Chem. Soc., 1992, 114, 767; 1992, 114, 3993; P. Magnus, C. Hulme and W. Weber, J. Am. Chem. Soc., 1994, 116, 4501; P. Magnus, J. Lacour, P. A. Evans, M. B. Roe and C. Hulme, J. Am. Chem. Soc., 1996, 118, 3406.