Diastereospecific synthesis of enantiomerically pure polysubstituted azetidines from 1,3-amino alcohols with three chiral centers

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5659-5662

  Barluenga, José ^a   Fernández Marí, Félix ^a   Viado, Argimiro L ^a   Aguilar, Enrique ^a   Olano, Bernardo ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001329641     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960494b     Document Type: Article

References (32)

1. (a) Testa, E.; Wittigens, A.; Maffii, G.; Bianchi, G. in Research Progress in Organic, Biological and Medicinal Chemistry; Gallo, U., Santamaria, L., Eds.; North-Holland Publishing Co.; Amsterdam, 1964; Vol 1, p 477.
2. (b) Okutani, T.; Kaneko, T.; Masuda, K. Chem. Pharm. Bull. 1974, 22, 1490.
3. (c) Kobayashi, J.; Cheng, J.; Ishibashi, M.; Wälchli, M. P.; Yamamura, S.; Ohizumi, Y. J. Chem. Soc., Perkin Trans. 1 1991, 1135.
4. (d) Frigola, J.; Torrens, A.; Castrillo, J. A.; Mas, J.; Vañó, D.; Berrocal, J. M.; Calvet, C.; Salgado, L.; Redondo, J.; García-Granda, S.; Valentí, E.; Quintana, J. R. J. Med. Chem. 1994, 37, 4195 and references cited therein.
5. For reviews see: (a) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. (b) Moore, J. A.; Ayers, R. S. In Small Ring Heterocycles; Hassner, A., Ed.; Wiley; New York, 1983; Part 2, p 1. (c) Davies, D. E.; Storr, R. C. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon; Oxford, 1984; Vol 7, p 237.
6. For reviews see: (a) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. (b) Moore, J. A.; Ayers, R. S. In Small Ring Heterocycles; Hassner, A., Ed.; Wiley; New York, 1983; Part 2, p 1. (c) Davies, D. E.; Storr, R. C. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon; Oxford, 1984; Vol 7, p 237.
7. For reviews see: (a) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331. (b) Moore, J. A.; Ayers, R. S. In Small Ring Heterocycles; Hassner, A., Ed.; Wiley; New York, 1983; Part 2, p 1. (c) Davies, D. E.; Storr, R. C. In Comprehensive Heterocyclic Chemistry; Lwowski, W., Ed.; Pergamon; Oxford, 1984; Vol 7, p 237.
8. (a) Rama Rao, A. V.; Gurjar, M. K.; Kaiwar, V. Tetrahedron: Asymmetry 1992, 3, 859.
9. (b) Kozikowski, A. P.; Tückmantel, W.; Liao, Y.; Manev, H.; Ikonomovic, S.; Wroblewski, J. T. J. Med. Chem. 1993, 36, 2706.
10. (c) Guanti, G.; Riva, R. Tetrahedron: Asymmetry 1995, 6, 2921.
11. (a) Duréault, A.; Portal, M.; Carreaux, F.; Depezay, J. C. Tetrahedron 1993, 49, 4201.
12. (b) Hoshino, J.; Hiraoka, J.; Hata, Y.; Sawada, S.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1995, 693.
13. (a) Poch, M.; Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 6935.
14. (b) Hiraki, T.; Yamagiwa, Y.; Kamikawa, T. Tetrahedron Lett. 1995, 36, 4841.
15. (a) Yamashita, M.; Ojima, I. J. Am. Chem. Soc. 1983, 105, 6339.
16. (b) Ojima, I.; Zhao, M.; Yamato, T.; Nakahashi, K. J. Org. Chem. 1991, 56, 5263.
17. (c) Shustov, G. V.; Rauk, A. J. Am. Chem. Soc. 1995, 117, 928.
18. (a) Barluenga, J.; Olano, B.; Fustero, S. J. Org. Chem. 1985, 50, 4052.
19. (b) Barluenga, J.; Joglar, J.; González, F. J.; Fustero, S. Tetrahedron Lett. 1989, 30, 2001.
20. (c) Barluenga, J.; Aguilar, E.; Olano, B.; Fustero, S. Synlett 1990, 463.
21. (d) Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. L. J. Org. Chem. 1992, 57, 1219.
22. Barluenga, J.; Olano, B.; Fustero, S.; Foces-Foces, M. C.; Cano, F. H. J. Chem. Soc., Chem. Commun. 1988, 410.
23. Barluenga, J.; Viado, A. L.; Aguilar, E.; Fustero, S.; Olano, B. J. Org. Chem. 1993, 58, 5972.
24. (a) Stevens, M. F.; Cromwell, N. H. J. Heterocyc. Chem. 1971, 8, 253.
25. (b) Kurteva, V. B.; Lyapova, M. J.; Pojarlieff, I. G. J. Chem. Res. (S) 1993, 270.
26. For mechanistic considerations, see: Vaughan, W. R.; Klonowski, R. S.; McElhinney, R. S.; Millward, B. B. J. Org. Chem. 1961, 26, 138.
27. N1 processes even more and increases rupture and elimination processes so much that only 10% of trans,cis-6d or 33% of trans,trans-6d are obtained.
28. The inversion of configuration detected in the cyclization of an anti-amino alcohol is remarkable, despite formation of a hindered cis-azetidine, which has also been observed in ref 5b. In our case, the presence of an aryl group in the hydroxylic carbon would explain the formation of a little amount of the trans-azetidine even in a very little polar solvent (see Table 2, entry 6 and footnote f).
29. (a) Axenrod, T.; Watnick, C.; Yazdekhasti, H.; Dave, P. R. Tetrahedron Lett. 1993, 34, 6677.
30. (b) Huszthy, P.; Bradshaw, J. S.; Krakowiak, K. E.; Wang, T.; Dalley, N. K. J. Heterocyc. Chem. 1993, 30, 1197.
31. Batterham, T. J. NMR Spectra of Simple Heterocycles; Wiley; New York, 1973; p 144.
32. Barluenga, J.; Olano, B.; Fustero, S. J. Org. Chem. 1983, 48, 2255.