Dicobalt Octacarbonyl Promoted Rearrangement of 4-Isoxazolines to Acylaziridines: Dramatic Rate Acceleration with Very High Substrate Tolerance

Organic Letters

Volumn 4, Issue 11, 2002, Pages 1907-1910

  Ishikawa, Teruhiko ^a   Kudoh, Takayuki ^a   Yoshida, Juri ^a   Yasuhara, Ayako ^a   Manabe, Shinobu ^a   Saito, Seiki ^a  

^a OKAYAMA UNIVERSITY   (Japan)

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EID: 0000684875     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025906j     Document Type: Article

References (35)

1. Baldwin, J. E.; Pudussery, R. G.; Qureshi, A. K.; Sklarz, B. J. Am. Chem. Soc. 1968, 90, 5325-5326.
2. (a) Freeman, J. P. Chem. Rev. 1983, 83, 241-261.
3. (b) For N-methoxy-4-isoxazoline to N-methoxyaziridine transformation, see: Grëe, R.; Carrie, R. J. Am. Chem. Soc. 1977, 99, 6667-6672.
4. (c) Shim, J.; Houk. K. N. J. Am. Chem. Soc. 1973, 95, 5798-5800.
5. (d) For isoxazolidinone to aziridine transformation, see: Chidichimo, G.; Gum, G.; Lelj, F.; Uccella, N. J. Am. Chem. Soc. 1980, 102, 1372-1377. The rearrangement took place, in general, when a substituent on the nitrogen atom was a phenyl, tert-butyl, or methoxy group except for the case in which X or Y was an electron-withdrawing group.
6. For reviews on reactions of aziridines, see: (a) Mitunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.3. (b) Padwa. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 4.9. (c) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 4.1. (d) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 8.1. (e) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
7. For reviews on reactions of aziridines, see: (a) Mitunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.3. (b) Padwa. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 4.9. (c) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 4.1. (d) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 8.1. (e) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
8. For reviews on reactions of aziridines, see: (a) Mitunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.3. (b) Padwa. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 4.9. (c) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 4.1. (d) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 8.1. (e) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
9. For reviews on reactions of aziridines, see: (a) Mitunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.3. (b) Padwa. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 4.9. (c) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 4.1. (d) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 8.1. (e) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
10. For reviews on reactions of aziridines, see: (a) Mitunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, Chapter 1.3. (b) Padwa. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 4.9. (c) Thompson, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 4.1. (d) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 8.1. (e) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
11. For leading references for aziridine synthesis, see: (a) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.5. (b) Reference 3e. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (d) Wulff, W. D.; Antilla, J. C. Angew. Chem., Int. Ed. 2000, 39, 4518-4521. (e) Hada, K.; Watanabe, T.; Isobe, T.; Ishikawa, T. J. Am. Chem. Soc. 2001, 123, 7705-7706. (f) Dauban, P.; Saniélie, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
12. For leading references for aziridine synthesis, see: (a) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.5. (b) Reference 3e. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (d) Wulff, W. D.; Antilla, J. C. Angew. Chem., Int. Ed. 2000, 39, 4518-4521. (e) Hada, K.; Watanabe, T.; Isobe, T.; Ishikawa, T. J. Am. Chem. Soc. 2001, 123, 7705-7706. (f) Dauban, P.; Saniélie, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
13. For leading references for aziridine synthesis, see: (a) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.5. (b) Reference 3e. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (d) Wulff, W. D.; Antilla, J. C. Angew. Chem., Int. Ed. 2000, 39, 4518-4521. (e) Hada, K.; Watanabe, T.; Isobe, T.; Ishikawa, T. J. Am. Chem. Soc. 2001, 123, 7705-7706. (f) Dauban, P.; Saniélie, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
14. For leading references for aziridine synthesis, see: (a) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.5. (b) Reference 3e. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (d) Wulff, W. D.; Antilla, J. C. Angew. Chem., Int. Ed. 2000, 39, 4518-4521. (e) Hada, K.; Watanabe, T.; Isobe, T.; Ishikawa, T. J. Am. Chem. Soc. 2001, 123, 7705-7706. (f) Dauban, P.; Saniélie, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
15. For leading references for aziridine synthesis, see: (a) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.5. (b) Reference 3e. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (d) Wulff, W. D.; Antilla, J. C. Angew. Chem., Int. Ed. 2000, 39, 4518-4521. (e) Hada, K.; Watanabe, T.; Isobe, T.; Ishikawa, T. J. Am. Chem. Soc. 2001, 123, 7705-7706. (f) Dauban, P.; Saniélie, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
16. For leading references for aziridine synthesis, see: (a) Kemp, J. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 7, Chapter 3.5. (b) Reference 3e. (c) Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728. (d) Wulff, W. D.; Antilla, J. C. Angew. Chem., Int. Ed. 2000, 39, 4518-4521. (e) Hada, K.; Watanabe, T.; Isobe, T.; Ishikawa, T. J. Am. Chem. Soc. 2001, 123, 7705-7706. (f) Dauban, P.; Saniélie, L.; Tarrade, A.; Dodd, R. H. J. Am. Chem. Soc. 2001, 123, 7707-7708.
17. Aschwanden, P.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2000, 2, 2331-2333.
18. Nitta, M.; Kobayashi, T. J. Chem. Soc., Perkin Trans, 1 1985, 1401-1406.
19. (Matrix Presented)
20. No reaction occurred below 70 °C.
21. Synthetic procedures of 1 are provided in Supporting Information.
22. For the preparation of 4, see: Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1995, 1171-1173.
23. This process opens a general strategy for the synthesis of chiral aziridines from chiral isoxazolidinones. For the asymmetric synthesis of isoxazolidinones, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291-1293. (b) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393-3396 and references therein.
24. This process opens a general strategy for the synthesis of chiral aziridines from chiral isoxazolidinones. For the asymmetric synthesis of isoxazolidinones, see: (a) Ishikawa, T.; Nagai, K.; Kudoh, T.; Saito, S. Synlett 1998, 1291-1293. (b) Sibi, M. P.; Liu, M. Org. Lett. 2000, 2, 3393-3396 and references therein.
25. The generation of azomethine ylide intermediates from 2 or 3 under the given conditions might be responsible for the low yield of 2 (or 3) (entries 1, 6, and 10 in Table 1 and 2m in Scheme 1). In fact a solution of 2f in benzene at 80 °C for 12 h in the presence of ethyl propiolate afforded substituted pyrrole 5 apparently through regioselective [1,3]-dipolar cycloaddition of azomethine ylide (C) followed by oxidation. (Matrix Presented) For azomethine ylide formation, see: (a) Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A.; McPhail, A. T. J. Org. Chem. 1985, 50, 4114-4119. (b) Vedejs, E.; Grissom, J. W. J. Am. Chem. Soc. 1988, 110, 3238-3246 and references therein. See also: (c) L.-Calle, E.; Eberbach, W. J. Chem. Soc., Chem. Commun. 1994, 301-302.
26. The generation of azomethine ylide intermediates from 2 or 3 under the given conditions might be responsible for the low yield of 2 (or 3) (entries 1, 6, and 10 in Table 1 and 2m in Scheme 1). In fact a solution of 2f in benzene at 80 °C for 12 h in the presence of ethyl propiolate afforded substituted pyrrole 5 apparently through regioselective [1,3]-dipolar cycloaddition of azomethine ylide (C) followed by oxidation. (Matrix Presented) For azomethine ylide formation, see: (a) Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A.; McPhail, A. T. J. Org. Chem. 1985, 50, 4114-4119. (b) Vedejs, E.; Grissom, J. W. J. Am. Chem. Soc. 1988, 110, 3238-3246 and references therein. See also: (c) L.-Calle, E.; Eberbach, W. J. Chem. Soc., Chem. Commun. 1994, 301-302.
27. The generation of azomethine ylide intermediates from 2 or 3 under the given conditions might be responsible for the low yield of 2 (or 3) (entries 1, 6, and 10 in Table 1 and 2m in Scheme 1). In fact a solution of 2f in benzene at 80 °C for 12 h in the presence of ethyl propiolate afforded substituted pyrrole 5 apparently through regioselective [1,3]-dipolar cycloaddition of azomethine ylide (C) followed by oxidation. (Matrix Presented) For azomethine ylide formation, see: (a) Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A.; McPhail, A. T. J. Org. Chem. 1985, 50, 4114-4119. (b) Vedejs, E.; Grissom, J. W. J. Am. Chem. Soc. 1988, 110, 3238-3246 and references therein. See also: (c) L.-Calle, E.; Eberbach, W. J. Chem. Soc., Chem. Commun. 1994, 301-302.
28. 8 with acetonitrile. When the evolution of CO ceased, the mixture turned out to be useless for the rearrangement. Therefore, the cobalt complex should be added to a solution of 1 in acetonitrile.
29. For the mechanism of the thermal rearrangement of 1 with an N-aryl or N-methoxy substituent to 2-acylaziridines, three possibilities have been proposed involving concerted, zwitterionic, or biradical processes. See ref 2.
30. 8 on treatment with a weak base. See: Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 64, 2164-2165.
31. 8 on treatment with a weak base. See: Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 64, 2164-2165.
32. 8 on treatment with a weak base. See: Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 64, 2164-2165.
33. 8 on treatment with a weak base. See: Hinterding, K.; Jacobsen, E. N. J. Org. Chem. 1999, 64, 2164-2165.
34. For other examples of the rearrangement involving N-O bond cleavage processes, see: (a) Hutchins, C. W.; Coates, R. M. J. Org. Chem. 1979, 44, 4742-4744. (b) Padwa, A.; Wong, G. S. K. J. Org. Chem. 1986, 51, 3125-3133.
35. For other examples of the rearrangement involving N-O bond cleavage processes, see: (a) Hutchins, C. W.; Coates, R. M. J. Org. Chem. 1979, 44, 4742-4744. (b) Padwa, A.; Wong, G. S. K. J. Org. Chem. 1986, 51, 3125-3133.