Stereoselective synthesis of enantiopure 6-fluoromethyl furo[3,4-c]- isoxazolidines

Synthetic Communications

Volumn 28, Issue 14, 1998, Pages 2665-2677

  Bandiera, Paola ^a   Bravo, Pierfrancesco ^a   Bruché, Luca ^a   Zanda, Matteo ^a   Arnone, Alberto ^b  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

6 FLUOROMETHYLFURO[3,4 C]ISOXAZOLIDINE; ISOXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031857712     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004836     Document Type: Article

References (28)

1. "1,3-Dipolar Cycloaddition Chemistry," Padwa, A., ed, Wiley, New York, 1984; Carruthers, W. "Cycloaddition Reactions in Organic Synthesis," Pergamon Press, Oxford, 1990.
2. "1,3-Dipolar Cycloaddition Chemistry," Padwa, A., ed, Wiley, New York, 1984; Carruthers, W. "Cycloaddition Reactions in Organic Synthesis," Pergamon Press, Oxford, 1990.
3. (a) Torssell, K.B.G. "Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis," VCH, New York, 1988, p. 25;
4. (b) Annunziata, R., Cinquini, M., Cozzi, F. and Raimondi, L. Gazz. Chim. Ital., 1989, 119, 253; Cinquini, M. and Cozzi, F. in "Houben-Weyl, Methods of Organic Chemistry: Stereoselective Synthesis", Helmchen, G., Hoffmann, R.W., Mulzer, J. and Schaumann, E., eds., Thieme, Stuttgart, New York, 1995, vol. E21c, ch. 1.6.1.2; Frederickson, M. Tetrahedron 1997, 53, 403.
5. (b) Annunziata, R., Cinquini, M., Cozzi, F. and Raimondi, L. Gazz. Chim. Ital., 1989, 119, 253; Cinquini, M. and Cozzi, F. in "Houben-Weyl, Methods of Organic Chemistry: Stereoselective Synthesis", Helmchen, G., Hoffmann, R.W., Mulzer, J. and Schaumann, E., eds., Thieme, Stuttgart, New York, 1995, vol. E21c, ch. 1.6.1.2; Frederickson, M. Tetrahedron 1997, 53, 403.
6. (b) Annunziata, R., Cinquini, M., Cozzi, F. and Raimondi, L. Gazz. Chim. Ital., 1989, 119, 253; Cinquini, M. and Cozzi, F. in "Houben-Weyl, Methods of Organic Chemistry: Stereoselective Synthesis", Helmchen, G., Hoffmann, R.W., Mulzer, J. and Schaumann, E., eds., Thieme, Stuttgart, New York, 1995, vol. E21c, ch. 1.6.1.2; Frederickson, M. Tetrahedron 1997, 53, 403.
7. (a) Tamura, O., Okabe, T., Yamaguchi, T., Kotani, J., Gotanda, K. and Sakamoto, M. Tetrahedron 1995, 51, 119 and references cited therein; Jung, M.E. and Vu, B.T. J.Org.Chem. 1996, 61, 4427; Jiang, S., McCullough, K.J., Mekki, B., Singh, G. and Wightman, R.H. J.Chem.Soc., Perkin Trans. 1 1997, 1805; Tamura, O., Mita, N., Kusaka, N., Suzuki, H. and Sakamoto, M. Tetrahedron Lett. 1997, 38, 429; Aurich, H.G., Geiger, M. and Sievers, U. Synlett. 1997, 1004; Namboothiri, I.N.N., Hassner, A. and Gottlieb, H.E. J.Org.Chem. 1997, 62, 485;
8. (a) Tamura, O., Okabe, T., Yamaguchi, T., Kotani, J., Gotanda, K. and Sakamoto, M. Tetrahedron 1995, 51, 119 and references cited therein; Jung, M.E. and Vu, B.T. J.Org.Chem. 1996, 61, 4427; Jiang, S., McCullough, K.J., Mekki, B., Singh, G. and Wightman, R.H. J.Chem.Soc., Perkin Trans. 1 1997, 1805; Tamura, O., Mita, N., Kusaka, N., Suzuki, H. and Sakamoto, M. Tetrahedron Lett. 1997, 38, 429; Aurich, H.G., Geiger, M. and Sievers, U. Synlett. 1997, 1004; Namboothiri, I.N.N., Hassner, A. and Gottlieb, H.E. J.Org.Chem. 1997, 62, 485;
9. (a) Tamura, O., Okabe, T., Yamaguchi, T., Kotani, J., Gotanda, K. and Sakamoto, M. Tetrahedron 1995, 51, 119 and references cited therein; Jung, M.E. and Vu, B.T. J.Org.Chem. 1996, 61, 4427; Jiang, S., McCullough, K.J., Mekki, B., Singh, G. and Wightman, R.H. J.Chem.Soc., Perkin Trans. 1 1997, 1805; Tamura, O., Mita, N., Kusaka, N., Suzuki, H. and Sakamoto, M. Tetrahedron Lett. 1997, 38, 429; Aurich, H.G., Geiger, M. and Sievers, U. Synlett. 1997, 1004; Namboothiri, I.N.N., Hassner, A. and Gottlieb, H.E. J.Org.Chem. 1997, 62, 485;
10. (a) Tamura, O., Okabe, T., Yamaguchi, T., Kotani, J., Gotanda, K. and Sakamoto, M. Tetrahedron 1995, 51, 119 and references cited therein; Jung, M.E. and Vu, B.T. J.Org.Chem. 1996, 61, 4427; Jiang, S., McCullough, K.J., Mekki, B., Singh, G. and Wightman, R.H. J.Chem.Soc., Perkin Trans. 1 1997, 1805; Tamura, O., Mita, N., Kusaka, N., Suzuki, H. and Sakamoto, M. Tetrahedron Lett. 1997, 38, 429; Aurich, H.G., Geiger, M. and Sievers, U. Synlett. 1997, 1004; Namboothiri, I.N.N., Hassner, A. and Gottlieb, H.E. J.Org.Chem. 1997, 62, 485;
11. (a) Tamura, O., Okabe, T., Yamaguchi, T., Kotani, J., Gotanda, K. and Sakamoto, M. Tetrahedron 1995, 51, 119 and references cited therein; Jung, M.E. and Vu, B.T. J.Org.Chem. 1996, 61, 4427; Jiang, S., McCullough, K.J., Mekki, B., Singh, G. and Wightman, R.H. J.Chem.Soc., Perkin Trans. 1 1997, 1805; Tamura, O., Mita, N., Kusaka, N., Suzuki, H. and Sakamoto, M. Tetrahedron Lett. 1997, 38, 429; Aurich, H.G., Geiger, M. and Sievers, U. Synlett. 1997, 1004; Namboothiri, I.N.N., Hassner, A. and Gottlieb, H.E. J.Org.Chem. 1997, 62, 485;
12. (a) Tamura, O., Okabe, T., Yamaguchi, T., Kotani, J., Gotanda, K. and Sakamoto, M. Tetrahedron 1995, 51, 119 and references cited therein; Jung, M.E. and Vu, B.T. J.Org.Chem. 1996, 61, 4427; Jiang, S., McCullough, K.J., Mekki, B., Singh, G. and Wightman, R.H. J.Chem.Soc., Perkin Trans. 1 1997, 1805; Tamura, O., Mita, N., Kusaka, N., Suzuki, H. and Sakamoto, M. Tetrahedron Lett. 1997, 38, 429; Aurich, H.G., Geiger, M. and Sievers, U. Synlett. 1997, 1004; Namboothiri, I.N.N., Hassner, A. and Gottlieb, H.E. J.Org.Chem. 1997, 62, 485;
13. (b) Arnone, A., Cavicchioli, M., Donadelli, A. and Resnati, G. Tetrahedron: Asymmetry 1994, 5, 1019.
14. (a) Silvester, M.J., Aldrichim. Acta 1991, 24, 31; "Biomedical Aspects of Fluorine Chemistry," Filler, R. and Kobayashi, A., eds, Elsevier, New York, 1992;
15. (a) Silvester, M.J., Aldrichim. Acta 1991, 24, 31; "Biomedical Aspects of Fluorine Chemistry," Filler, R. and Kobayashi, A., eds, Elsevier, New York, 1992;
16. (b) for recent reviews on fluoroheterocycles see: Silvester, M.J. Adv. Heterocycl. Chem., 1994, 59, 1; Burger, K., Wucherpfennig, U. and Brunner, E. Adv. Heterocycl. Chem., 1994, 60, 1.
17. (b) for recent reviews on fluoroheterocycles see: Silvester, M.J. Adv. Heterocycl. Chem., 1994, 59, 1; Burger, K., Wucherpfennig, U. and Brunner, E. Adv. Heterocycl. Chem., 1994, 60, 1.
18. Bravo, P., Bruché, L., Farina, A., Fronza, G., Meille, S.V. and Merli, A. Tetrahedron: Asymmetry, 1993, 4, 2131; Bravo, P., Bruché, L., Fronza, G. and Merli, A. Gazz. Chim. Ital., 1994, 124, 275; Bravo, P., Bruché, L., Crucianelli, M., Farina, A., Meille, S.V., Merli, A. and Seresini, P., J. Chem. Res. 1996, (S) 348, (M) 1901.
19. Bravo, P., Bruché, L., Farina, A., Fronza, G., Meille, S.V. and Merli, A. Tetrahedron: Asymmetry, 1993, 4, 2131; Bravo, P., Bruché, L., Fronza, G. and Merli, A. Gazz. Chim. Ital., 1994, 124, 275; Bravo, P., Bruché, L., Crucianelli, M., Farina, A., Meille, S.V., Merli, A. and Seresini, P., J. Chem. Res. 1996, (S) 348, (M) 1901.
20. Bravo, P., Bruché, L., Farina, A., Fronza, G., Meille, S.V. and Merli, A. Tetrahedron: Asymmetry, 1993, 4, 2131; Bravo, P., Bruché, L., Fronza, G. and Merli, A. Gazz. Chim. Ital., 1994, 124, 275; Bravo, P., Bruché, L., Crucianelli, M., Farina, A., Meille, S.V., Merli, A. and Seresini, P., J. Chem. Res. 1996, (S) 348, (M) 1901.
21. Sugihara, H., Tanigaka, R. and Kaji, A. Synthesis 1978, 881.
22. Amone, A., Bandiera, P., Bravo, P., Bruché, L. and Zanda, M. Gazz.Chim.Ital. 1996, 126, 773.
23. Aurich, H.G. and Biesemeier, F. Synthesis 1995, 1171.
24. Bravo, P., Piovosi. E., Resnati, G. and De Munari, S. Gazz.Chim.Ital. 1988, 118, 115.
25. Bravo, P. and Resnati, G. Tetrahedron Lett. 1987, 28, 4856.
26. Arnone, A., Bravo, P., Viani, F., Cavicchio, G., Crucianelli, M. and Marchetti, V. Tetrahedron 1993, 49, 4253.
27. Arnone, A., Bravo, P., Donadelli, A. and Resnati, G., Tetrahedron 1996, 52, 131.
28. Ref. 2a, p. 14.