Ytterbium triflate catalyzed ring opening of aziridines with amines

Heterocycles

Volumn 43, Issue 11, 1996, Pages 2473-2482

  Meguro, Masaki ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000037474     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-7575     Document Type: Article

References (29)

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17. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
18. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
19. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
20. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
21. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
22. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
23. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
24. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
25. 3 with amines, see a)G. Jenner, Tetrahedron Lett., 1996, 37, 3691. b) H. Kotsuki, M. Teraguchi, N. Shimomoto and M. Ochi, ibid., 1996, 37, 3727. c) S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu and A. R. Katritzky, ibid., 1996, 37, 3731. d) P. G. Cozzi, B. D. Simone and A. Umani-Ronchi, ibid., 1996, 37, 1691. e) S. Kobayashi, M. Araki and M. Yasuda, ibid., 1995, 36, 5773. f) S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379. g) G. Jenner, Tetrahedron Lett., 1995, 36, 233. h) N. Yamamoto and M. Isobe, Chem. Lett., 1994, 2299. i) S. Matsubara, M. Yoshioka and K. Utimoto, ibid. 1994, 827. See also ref. 14.
26. 4 and LiOTf) and TfOH were found to be less efficient. M. Meguro and Y. Yamamoto, Unpublished results.
27. In the reaction of N-ethoxycarbonylaziridine with lithium amide, basic amide reagent attacked carbonyl group to give aziridine urea. See, A. Hassner and A. Kascheres, Tetrahedron Lett., 1970, 4623.
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