T-BuOK-Mediated Iodoaziridination Reaction of N-Allylic Tosylamide Derivatives

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4842-4845

  Kitagawa, Osamu ^a   Suzuki, Takashi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001319839     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980371m     Document Type: Article

References (28)

1. (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1984; Vol. 3, p 411.
2. (b) Gardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
3. (c) Harding, K. E.; Tiner, T. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, p 363.
4. Examples of haloepoxidation reactions of allyl alcohol derivatives which proceed via an ionic mechanism: (a) Winstein, S.; Goodman, L. J. Am. Chem. Soc. 1954, 76, 4368. (b) Ganem, B. J. Am. Chem. Soc. 1976, 98, 858. (c) Midland, M. M.; Halterman, R. J. Org. Chem. 1981, 46, 1227. (d) Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862.
5. Examples of haloepoxidation reactions of allyl alcohol derivatives which proceed via an ionic mechanism: (a) Winstein, S.; Goodman, L. J. Am. Chem. Soc. 1954, 76, 4368. (b) Ganem, B. J. Am. Chem. Soc. 1976, 98, 858. (c) Midland, M. M.; Halterman, R. J. Org. Chem. 1981, 46, 1227. (d) Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862.
6. Examples of haloepoxidation reactions of allyl alcohol derivatives which proceed via an ionic mechanism: (a) Winstein, S.; Goodman, L. J. Am. Chem. Soc. 1954, 76, 4368. (b) Ganem, B. J. Am. Chem. Soc. 1976, 98, 858. (c) Midland, M. M.; Halterman, R. J. Org. Chem. 1981, 46, 1227. (d) Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862.
7. Examples of haloepoxidation reactions of allyl alcohol derivatives which proceed via an ionic mechanism: (a) Winstein, S.; Goodman, L. J. Am. Chem. Soc. 1954, 76, 4368. (b) Ganem, B. J. Am. Chem. Soc. 1976, 98, 858. (c) Midland, M. M.; Halterman, R. J. Org. Chem. 1981, 46, 1227. (d) Evans, R. D.; Magee, J. W.; Schauble, J. H. Synthesis 1988, 862.
8. Haloepoxide-forming reaction from allyl alcohol derivatives under radical conditions has been also reported; see: (a) Suginome, H.; Wang, J. B. J. Chem. Soc., Chem. Commun. 1990, 1629. (b) Galatsis, P.; Millan, S. D.; Tetrahedron Lett. 1991, 32, 7493. (c) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687.
9. Haloepoxide-forming reaction from allyl alcohol derivatives under radical conditions has been also reported; see: (a) Suginome, H.; Wang, J. B. J. Chem. Soc., Chem. Commun. 1990, 1629. (b) Galatsis, P.; Millan, S. D.; Tetrahedron Lett. 1991, 32, 7493. (c) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687.
10. Haloepoxide-forming reaction from allyl alcohol derivatives under radical conditions has been also reported; see: (a) Suginome, H.; Wang, J. B. J. Chem. Soc., Chem. Commun. 1990, 1629. (b) Galatsis, P.; Millan, S. D.; Tetrahedron Lett. 1991, 32, 7493. (c) Rawal, V. H.; Iwasa, S. Tetrahedron Lett. 1992, 33, 4687.
11. Knipe, A. C.; Stirling, C. J. M. J. Chem. Soc. B 1968, 67.
12. 4-mediated iodocarbocyclization reaction of alkenylmalonates: (a) Taguchi, T.; Kitagawa, O.; Inoue, T. J. Synth. Org. Chem. Jpn. 1995, 53, 770. (b) Kitagawa, O.; Inoue, T.; Taguchi, T. Rev. Heteroat. Chem. 1996, 15, 243.
13. 4-mediated iodocarbocyclization reaction of alkenylmalonates: (a) Taguchi, T.; Kitagawa, O.; Inoue, T. J. Synth. Org. Chem. Jpn. 1995, 53, 770. (b) Kitagawa, O.; Inoue, T.; Taguchi, T. Rev. Heteroat. Chem. 1996, 15, 243.
14. (a) Kitagawa, O.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1992, 33, 2167.
15. (b) Inoue, T.; Kitagawa, O.; Ochiai, O.; Taguchi, T. Tetrahedron: Asymmetry 1995, 6, 691.
16. 2 and NaH: Beckwith, A. L.; Zozer, M. J. Tetrahedron Lett. 1992, 33, 4975.
17. Preliminary communication of this work: Kitagawa, O.; Suzuki, T.; Taguchi, T. Tetrahedron Lett. 1997, 38, 8371.
18. Preparation and utilization of aziridine derivatives: (a) Deyrup, J. A. In Small Ring Heterocyclic Chemistry; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 1, p 1. (b) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469 . (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
19. Preparation and utilization of aziridine derivatives: (a) Deyrup, J. A. In Small Ring Heterocyclic Chemistry; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 1, p 1. (b) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469 . (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
20. Preparation and utilization of aziridine derivatives: (a) Deyrup, J. A. In Small Ring Heterocyclic Chemistry; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 1, p 1. (b) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469 . (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
21. Preparation and utilization of aziridine derivatives: (a) Deyrup, J. A. In Small Ring Heterocyclic Chemistry; Hassner, A., Ed.; Wiley: New York, 1983; Vol. 1, p 1. (b) Kemp, J. E. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 469 . (c) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
22. Preparation of halomethylaziridines by other methods and their utilization: (a) Gensler, W. J. J. Am. Chem. Soc. 1948, 70, 1843. (b) Gensler, W. J.; Brooks, B. A. J. Org. Chem. 1966, 31, 568. (c) Kimpe, N. D.; Smaele, D. D.; Sakonyi, Z. J. Org. Chem. 1997, 62, 2448 and references cited therein.
23. Preparation of halomethylaziridines by other methods and their utilization: (a) Gensler, W. J. J. Am. Chem. Soc. 1948, 70, 1843. (b) Gensler, W. J.; Brooks, B. A. J. Org. Chem. 1966, 31, 568. (c) Kimpe, N. D.; Smaele, D. D.; Sakonyi, Z. J. Org. Chem. 1997, 62, 2448 and references cited therein.
24. Preparation of halomethylaziridines by other methods and their utilization: (a) Gensler, W. J. J. Am. Chem. Soc. 1948, 70, 1843. (b) Gensler, W. J.; Brooks, B. A. J. Org. Chem. 1966, 31, 568. (c) Kimpe, N. D.; Smaele, D. D.; Sakonyi, Z. J. Org. Chem. 1997, 62, 2448 and references cited therein.
25. 4: (a) Kitagawa, O.; Fujita, M.; Li, F.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615. (b) Fujita, M.; Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1997, 62, 7330.
26. 4: (a) Kitagawa, O.; Fujita, M.; Li, F.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615. (b) Fujita, M.; Kitagawa, O.; Suzuki, T.; Taguchi, T. J. Org. Chem. 1997, 62, 7330.
27. Haloaziridine product could not be obtained by the combination of t-BuOK and NBS or NIS.
28. Kitagawa, O.; Kikuchi, N.; Hanano, T.; Aoki, K.; Yamazaki, T.; Okada, M.; Taguchi, T. J. Org. Chem. 1995, 60, 7161.