Synthesis of enantiopure 2-azabicyclo[3.3.1]nonanes by a radical ring closure

Tetrahedron Asymmetry

Volumn 10, Issue 12, 1999, Pages 2399-2410

  Quirante, Josefina ^a   Torra, Mercè ^a   Diaba, Faïza ^a   Escolano, Carmen ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033580754     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00221-9     Document Type: Article

References (29)

1. Quirante, J.; Escolano, C.; Diaba, F.; Bonjoch, J. Heterocycles 1999, 50, 731-738.
2. (a) Quirante, J.; Escolano, C.; Massot, M.; Bonjoch, J. Tetrahedron 1997, 53, 1391-1402.
3. (b) Quirante, J.; Escolano, C.; Merino, A.; Bonjoch, J. J. Org. Chem. 1998, 63, 968-976.
4. (a) Quirante, J.; Escolano, C.; Costejá, L.; Bonjoch, J. Tetrahedron Lett. 1997, 38, 6901-6904.
5. (b) Quirante, J.; Escolano, C.; Diaba, F.; Bonjoch, J. J. Chem. Soc., Perkin Trans. 1 1999, 1157-1162.
6. 2b etc).
7. Fujii, K.; Sivonen, K.; Adachi, K.; Noguchi, K.; Shimizu, Y.; Sano, H.; Hirayama, K.; Suzuki, M.; Harada, K. Tetrahedron Lett. 1997, 38, 5529-5532.
8. Samamoto, E.; Tsujii, E.; Abe, F.; Nakanishi, T.; Yamashita, N.; Shigematsu, N.; Izumi, S.; Okuhara, M. J. Antibiot. 1996, 49, 37-44.
9. Kong, F.; Andersen, R. J. J. Am. Chem. Soc. 1994, 116, 6007-6008.
10. Sole, D.; Bonjoch, J.; García-Rubio, S.; Peidró, E.; Bosch, J. Angew. Chem., Int. Ed. Engl. 1999, 38, 395-397.
11. For recent synthesis in the racemic series, see: (a) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110. (b) Dondas, H. A.; Grigg, R.; Frampton, C. S. Tetrahedron Lett. 1997, 38, 5719-5722. (c) Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429. (d) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281. (e) Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403-406.
12. For recent synthesis in the racemic series, see: (a) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110. (b) Dondas, H. A.; Grigg, R.; Frampton, C. S. Tetrahedron Lett. 1997, 38, 5719-5722. (c) Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429. (d) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281. (e) Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403-406.
13. For recent synthesis in the racemic series, see: (a) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110. (b) Dondas, H. A.; Grigg, R.; Frampton, C. S. Tetrahedron Lett. 1997, 38, 5719-5722. (c) Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429. (d) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281. (e) Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403-406.
14. For recent synthesis in the racemic series, see: (a) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110. (b) Dondas, H. A.; Grigg, R.; Frampton, C. S. Tetrahedron Lett. 1997, 38, 5719-5722. (c) Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429. (d) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281. (e) Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403-406.
15. For recent synthesis in the racemic series, see: (a) Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron 1995, 51, 11087-11110. (b) Dondas, H. A.; Grigg, R.; Frampton, C. S. Tetrahedron Lett. 1997, 38, 5719-5722. (c) Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429. (d) Yamazaki, N.; Suzuki, H.; Kibayashi, C. J. Org. Chem. 1997, 62, 8280-8281. (e) Thomas, J. B.; Gigstad, K. M.; Fix, S. E.; Burgess, J. P.; Cooper, J. B.; Mascarella, S. W.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Tetrahedron Lett. 1999, 40, 403-406.
16. The preference of the two rotational isomers for each compound in this series is very sensitive to the substituent at C-4; compound 5: Z:E rotamers 1:3 ratio; compound 6: Z:E rotamers 7:3 ratio.
17. For examples in which radical translocation reactions occur and the behaviour of two rotamers is different, see: (a) Curran, D. P.; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1393. (b) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343-7366.
18. For examples in which radical translocation reactions occur and the behaviour of two rotamers is different, see: (a) Curran, D. P.; Liu, H. J. Chem. Soc., Perkin Trans. 1 1994, 1377-1393. (b) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343-7366.
19. For oxidative processes of a 1-amidoalkyl radical to the corresponding cation by action of a trichloroacetamide, see: Cassayre, J.; Quiclet-Sire, B.; Saunier, J.-B.; Zard, S. Z. Tetrahedron 1998, 54, 1029-1040. See also Ref. 11b.
20. For 5-exo-trig cyclization of N-allylic systems, see: (a) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663-2677. (b) Ishibashi, H.; Fuke, Y.; Yamashita, T.; Ikeda, M. Tetrahedron: Asymmetry 1996, 7, 2531-2538. (c) Ikeda, M.; Ohtani, S.; Sato, T.; Ishibashi, H. Synthesis 1998, 1803-1806.
21. For 5-exo-trig cyclization of N-allylic systems, see: (a) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663-2677. (b) Ishibashi, H.; Fuke, Y.; Yamashita, T.; Ikeda, M. Tetrahedron: Asymmetry 1996, 7, 2531-2538. (c) Ikeda, M.; Ohtani, S.; Sato, T.; Ishibashi, H. Synthesis 1998, 1803-1806.
22. For 5-exo-trig cyclization of N-allylic systems, see: (a) Cardillo, B.; Galeazzi, R.; Mobbili, G.; Orena, M.; Rossetti, M. Heterocycles 1994, 38, 2663-2677. (b) Ishibashi, H.; Fuke, Y.; Yamashita, T.; Ikeda, M. Tetrahedron: Asymmetry 1996, 7, 2531-2538. (c) Ikeda, M.; Ohtani, S.; Sato, T.; Ishibashi, H. Synthesis 1998, 1803-1806.
23. For 4-exo-trig cyclization of N-vinylic systems, see: (a) Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489-502. (b) Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867-13880. (c) Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611-9622.
24. For 4-exo-trig cyclization of N-vinylic systems, see: (a) Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489-502. (b) Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867-13880. (c) Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611-9622.
25. For 4-exo-trig cyclization of N-vinylic systems, see: (a) Ishibashi, H.; Kameoka, C.; Kodama, K.; Ikeda, M. Tetrahedron 1996, 52, 489-502. (b) Ishibashi, H.; Kodama, K.; Kameoka, C.; Kawanami, H.; Ikeda, M. Tetrahedron 1996, 52, 13867-13880. (c) Ishibashi, H.; Kameoka, C.; Kodama, K.; Kawanami, H.; Hamada, M.; Ikeda, M. Tetrahedron 1997, 53, 9611-9622.
26. Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 2183-2186.
27. Lemière, G. L.; Dommisse, R. A.; Lepoivre, J. A.; Alderweireldt, F. C.; Hiemstra, H.; Wynberg, H.; Jones, J. B.; Toone, E. J. J. Am. Chem. Soc. 1987, 109, 1363-1370.
28. 2), 54.2 (C-5), 55.9 (C-1), 67.1 (C-7), 77.6 and 78.9 (CH acetal), 110.6 (C-2), 125.3, 126.1, 127.4, 152.8 (Ar). The minor signals corresponding to the (1S,5R,1R) isomer are the following: 14.0, 16.8, 17.0, 21.7, 26.2, 29.7, 31.4, 38.4, 53.9, 55.3, 68.1, 77.2, 77.9, 110.2, 124.9, 126.0, 127.4 and 152.8.
29. Damm, W.; Giese, B.; Hasskerl, T.; Houk, K. N.; Hùter, O.; Zipse, H. J. Am. Chem. Soc. 1992, 114, 4067-4079.