Ring opening of phenylaziridines with allylsilanes

Tetrahedron Letters

Volumn 37, Issue 47, 1996, Pages 8493-8496

  Schneider, Marie Reine ^a   Mann, André ^a   Taddei, Maurizio ^b  

^a CENTRE DE NEUROCHIMIE   (France)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG IDENTIFICATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0030592795     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01975-2     Document Type: Article

References (20)

1. 1. Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
2. 2. Kozikowski, A. P.; Ishida, H.; Isobe, K. J. Org. Chem. 1979, 44, 2788-2790.
3. 3. Baldwin, J. E.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153-155.
4. 4. Osborn, H. M. I.; Sweeney, J. B.; Howson, B. Synlett 1993, 676-677.
5. 5. Ibuka, T.; Nakai, K.; Habashita, H.; Fujii, N.; Garrido, F.; Mann, A.; Chounan, Y.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 7421-7424.
6. 6. Ezquerra, J.; Pedregal, C.; Lamas, C.; Pastor, A.; Alvarez, P.; Vaquerro, J. J. Tetrahedron Lett. 1996, 37, 683-686.
7. 7. Ibuka, T.; Schoenfelder, A.; Bildstein, P.; Mann, A. Synth. Commun. 1995, 25, 1777-1782.
8. 8. Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316.
9. 9. Langkopf, E. Schinzer, D. Chem. Rev. 1995, 95, 1375-1408.
10. 10. Bergmeir, S. C.; Seth, P. P. Tetrahedron Lett. 1995, 36, 3793-3796.
11. 11. Evans, D. ; Faul, M. M.; Bilodeau, M. T. J. Org. Chem. 1991, 56, 6744-6746.
12. 3) δ 0.06 (s, 9H), 0.08 (s, 9H), 0.99 (dd, J = 14.5 and 2.5 Hz, 1H), 1.05 (dd, J= 14.5 and 2.5 Hz, 1H), 1.48 (dd, J = 14.5 and 3.5 Hz, 1H), 1.59 (dd, J = 12 and 2.5 Hz, 1H), 1.70 (q, J = 3 Hz, 1H), 1.76-1.86 (m, 2 H), 2.28-2.46 (m, 1H), 2.46 (s, 6H), 2.53-2.64 (m, 1 H), 2.95 (t, J = 10 Hz, 1H), 3.30 (t, J = 11.5 Hz, 1H), 3.40-3.57 (m, 1 H), 3.70-3.96 (m, 4H), 6.95-7.25 (m, 8H), 7.32-7.75 (m, 8H).
13. 13. Bac, N. V.; Langlois, Y. J. Am. Chem. Soc. 1982, 104, 7666-7667.
14. 14. Harmata, M.; Jones, D. E. Tetrahedron Lett. 1995, 36, 4769-4772.
15. 15. Osumi, K.; Sugimura, H. Tetrahedron Lett. 1995, 36, 5789-5792.
16. 16. Kiyooka, S.; Shiomi, Y.; Kira, H.; Kaneko, Y.; Tanimori, S. J. Org. Chem. 1994, 59, 1958-1960.
17. 17. Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229-4232.
18. 3) δ 90.9, 21.5, 47.1, 49. 5, 127.1, 128.8, 129.2, 129.7, 131.2, 132.7, 136.9, 137.1, 139.5, 143.5.
19. 19. Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
20. 20. Evans, D. ; Faul, M. M.; Bilodeau, M. T.; Andersen, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 15, 5328-5329.