Diastereoselective nitrilimine cycloaddition to the C=N bond of enantiopure 1,4-benzodiazepinones

Tetrahedron Asymmetry

Volumn 13, Issue 22, 2002, Pages 2491-2495

  Molteni, Giorgio ^a   Broggini, Gianluigi ^b   Pilati, Tullio ^c  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZODIAZEPINE DERIVATIVE; HYDRAZONE DERIVATIVE; IMINE; NITRILE;

ARTICLE; CHEMICAL BOND; CYCLOADDITION; DIASTEREOISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0037073328     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00663-8     Document Type: Article

References (29)

1. Collins A.N., Sheldrake G.M., Crosby J. Chirality in Industry. 1992;John Wiley & Sons, New York.
2. For recent books, see: (a) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; Wiley: New York, 2002; (b) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002.
3. For recent books, see: (a) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A.; Pearson, W. H., Eds.; Wiley: New York, 2002; (b) Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002.
4. For recent reviews, see: (a) Kanemasa, S. Synlett 2002, 1371; (b) Karlsson, S.; Högberg, E.-H. Org. Prep. Proc. Int. 2001, 33, 1032; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449; (d) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
5. For recent reviews, see: (a) Kanemasa, S. Synlett 2002, 1371; (b) Karlsson, S.; Högberg, E.-H. Org. Prep. Proc. Int. 2001, 33, 1032; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449; (d) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
6. For recent reviews, see: (a) Kanemasa, S. Synlett 2002, 1371; (b) Karlsson, S.; Högberg, E.-H. Org. Prep. Proc. Int. 2001, 33, 1032; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449; (d) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
7. For recent reviews, see: (a) Kanemasa, S. Synlett 2002, 1371; (b) Karlsson, S.; Högberg, E.-H. Org. Prep. Proc. Int. 2001, 33, 1032; (c) Gothelf, K. V.; Jørgensen, K. A. Chem. Commun. 2000, 1449; (d) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
8. Broggini G., Garanti L., Molteni G., Zecchi G. Tetrahedron: Asymmetry. 10:1999;487.
9. Broggini G., Garanti L., Molteni G., Pilati T., Ponti A., Zecchi G. Tetrahedron: Asymmetry. 10:1999;2203.
10. Molteni G., Pilati T. Tetrahedron: Asymmetry. 10:1999;3873.
11. Broggini G., Casalone G., Garanti L., Molteni G., Pilati T., Zecchi G. Tetrahedron: Asymmetry. 10:1999;4447.
12. Broggini G., Molteni G., Pilati T. Tetrahedron: Asymmetry. 11:2000;1975.
13. Broggini G., Molteni L., Garanti G., Pilati T. Synth. Commun. 31:2001;2649.
14. Broggini G., Molteni G., Pilati T., Zecchi G. Synth. Commun. 31:2001;3799.
15. Garanti L., Molteni G., Pilati T. Tetrahedron: Asymmetry. 13:2002;1285.
16. Broggini G., Garanti L., Molteni G., Pilati T. Tetrahedron: Asymmetry. 12:2001;1201.
17. Garanti L., Molteni G., Broggini G. J. Chem. Soc., Perkin Trans. 1. 2001;1816.
18. Essaber M., Baouid A., Hasnaoui A., Giorgi M., Pierrot M. Acta Crystallogr., Sect. C. C54:1998;519.
19. El Messaoudi T., El Messaoudi M., Zair T., Hasnaoui A., Esseffar M., Lavergne J.-P. Synth. Commun. 32:2002;1815.
20. Shawali A.S. Chem. Rev. 93:1993;2731.
21. Hester J.B., Rudzik A.D., Kamadar B.V. J. Med. Chem. 14:1971;1078.
22. Meguro K., Kuwada Y. Tetrahedron Lett. 10:1970;4039.
23. Mohiuddin G., Reddy P.S., Ahmed K., Ratnam C.V. Heterocycles. 24:1986;3489.
24. Waltser A., Fryer R.I. Bicyclic Diazepines. 1991;Wiley, New York.
25. Fusco R., Garanti L., Zecchi G. J. Org. Chem. 40:1975;1906.
26. Bourgois J., Bourgois M., Texier F. Bull. Soc. Chim. Fr. 1978;485.
27. El-Abadelah M.M., Hussein A.Q., Kamal M.R., Al-Adhami K.H. Heterocycles. 27:1988;917.
28. Altomare A., Cascarano G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori G., Camalli G. J. Appl. Crystallogr. 27:1994;435.
29. Sheldrick, G. M. SHELX-97: Program for the Refinement of Crystal Structures; University of Göttingen, Germany, 1997.