Developing Molecular Diversity in the Construction of a Family of Bicyclic Isoxazolines Scaffolds: Control of Regio-and Diastereoselectivities

European Journal of Organic Chemistry

Volumn , Issue 24, 2003, Pages 4777-4785

  Giorgi, Gianluca ^a   Lampariello, L Raffaella ^b   Minetto, Giacomo ^b   Paoli, M Laura ^b   Riello, Vincenzo ^b   Rodriquez, Manuela ^b   Sega, Alessandro ^b  

^a Ctro Interdipartimentale Analisi D   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

Diastereoselectivity; Isoxazolines; Molecular diversity; Regioselectivity

Indexed keywords

BICYCLO COMPOUND; CYCLOPENTENE DERIVATIVE; CYCLOPENTENONE DERIVATIVE; FUNCTIONAL GROUP; ISOXAZOLINE DERIVATIVE; NITRILE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DEHYDROGENATION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0346732150     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300480     Document Type: Article

References (31)

1. A. P. Kozikowski, Acc. Chem. Res. 1984, 17, 410-416.
2. K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, VCH Publishers: New York, 1988.
3. M. J. Tronchet, S. Jaccard-Thorndahl, L. Faivre, L. Massard, Helv. Chim. Acta 1973, 56, 1303-1309.
4. A. A. Hagendorn III, B. J. Miller, J. O. Nagy, Tetrahedron Lett. 1980, 21, 229-230.
5. P. G. Baraldi, A. Barco, S. Benetti, G. B. Pollini, D. Simoni, Synthesis 1987, 857-869.
6. V. Jäger, D. Schröter, Synthesis 1990, 556-560.
7. M. De Amici, P. Magri, C. De Micheli, F. Cateni, R. Bovara, G. Carrea, G. Casalone, J. Org. Chem. 1992, 57, 2825-2829.
8. J. W. Patterson, P. S. Cheung, M. J. Ernest, J. Med. Chem. 1992, 35, 507-510.
9. F. Lepage, F. Tombret, G. Curier, A. Marivain, J. M. Gillardin, Eur. J. Med. Chem. 1992, 27, 581-593.
10. Y. Xiang, J. Chen, R. F. Schinazi, K. Zhao, Bioorg. & Med. Chem. 1996, 6, 1051-1054.
11. H. Gi, Y. Xiang, J. Chen, R. F. Schinazi, K. Zhao, J. Org. Chem. 1997, 62, 88-92.
12. G. Adembri, G. Giorgi, R. L. Lampariello, M. L. Paoli, A. Sega, J. Chem. Soc., Perkin Trans. 1 2000, 2649-2656.
13. G. Adembri, M. L. Paoli, A. Sega, J. Chem. Research (S) 2003, 126-127.
14. C. H. De Puy, C. E. Lyons, J. Am. Chem. Soc. 1960, 82, 631-633.
15. W. Herz, M. G. Nair, J. Org. Chem. 1969, 34, 4016-4023.
16. W. T. Comer, D. L. Temple, J. Org. Chem. 1973, 38, 2121-2125.
17. R. Subramanyan, P. D. Bartlett, G. Y. Moltrasio, W. H. Iglesias Watson, J. Galloy, J. Org. Chem. 1982, 47, 4491-4498.
18. H.-J. Lu, M. Llinas-Brunet, Can. J. Chem. 1984, 62, 1747-1750.
19. G. Cardinale, J. A. M. Laan, J. P. Ward, Recl. Trav. Chim. Pays-Bas 1987, 106, 62-68.
20. L. A. Paquette, C. Vannucci, R. D. Rogers, J. Am. Chem Soc. 1989, 111, 5792-5800.
21. A. A. M. Houwen-Claassen, A. J. H. Klunder, M. G. Kooy, J. Steffann, B. Zwanenburg, Tetrahedron 1989, 45, 7109-7133.
22. R. J. Heffner, M. M. Joullié, Synth. Commun. 1991, 21, 1055-1069.
23. B. Pandey, P. V. Dalri, Angew. Chem. Int. Ed. Engl. 1993, 32, 1612-1613.
24. P. Riviere, A. Mauvais, E. Winterfeldt, Tetrahedron: Asymmetry 1994, 5, 1831-1846.
25. F. J. A. D. Bakkaren, N. G. Ramesh, D. de Groot, A. J. H. Klunder, B. Zwanenburg, Tetrahedron Lett. 1996, 37, 8003-8006.
26. N. G. Ramesh, F. J. A. D. Bakkaren, D. de Groot, U. Passamonti, A. J. H. Klunder, B. Zwanenburg, Tetrahedron 2001, 57, 9877-9887.
27. N. Barbulescu, P. Grünanger, M. R. Langella, A. Quilico, Tetrahedron Lett. 1961, 89-91.
28. C. H. De Puy, E. F. Zaweski, J. Am. Chem. Soc. 1959, 81, 4920-4924.
29. G. Bianchi, C. De Micheli, R. Gandolfi, P. Grünanger, P. Vita-Finzi, O. V. de Pava, J. Chem. Soc., Perkin Trans. 1 1973, 1148-1155.
30. G. M. Sheldrick, SHELX-97, Rel. 97-2, University of Göttingen, 1997.
31. L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837-838.