Stereoselective 1,3-Dipolar Cycloadditions of Nitrile Oxides to Chiral (E)-1-Ethoxy-3-fluoroalkyl-3-hydroxy-4-(4-methylphenylsulfinyl)but-1-enes

Journal of Chemical Research - Part S

Volumn , Issue 4, 1996, Pages 198-199

  Arnone, Alberto ^a   Bravo, Pierfrancesco ^b   Bruché, Luca ^b   Seresini, Paolo ^b  

^a CNR   (Italy)

^b POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742571879     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. (a) 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984;
2. (b) W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990;
3. (c) K. B. G. Torssell, Nitrile Oxides, Nitrones and Nitronales in Organic Synthesis, VCH, New York, 1988.
4. (a) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 (and references therein);
5. (b) T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry, 1991, 2, 1479; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473; S. Kanemasa and K. Onimura, Tetrahedron, 1992, 40, 8645; C. Louis and C. Hootelé, Tetrahedron: Asymmetry, 1995, 9, 2149.
6. (b) T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry, 1991, 2, 1479; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473; S. Kanemasa and K. Onimura, Tetrahedron, 1992, 40, 8645; C. Louis and C. Hootelé, Tetrahedron: Asymmetry, 1995, 9, 2149.
7. (b) T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry, 1991, 2, 1479; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473; S. Kanemasa and K. Onimura, Tetrahedron, 1992, 40, 8645; C. Louis and C. Hootelé, Tetrahedron: Asymmetry, 1995, 9, 2149.
8. (b) T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry, 1991, 2, 1479; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473; S. Kanemasa and K. Onimura, Tetrahedron, 1992, 40, 8645; C. Louis and C. Hootelé, Tetrahedron: Asymmetry, 1995, 9, 2149.
9. Biomedical Aspects of Fluorine Chemistry, ed. R. Filler and Y. Kobayashi, Elsevier, New York, 1992; J. M. Silvester, Aldrichim. Acta, 1991, 24, 31; M. J. Silvester, Adv. Heterocycl. Chem., 1994. 59, 1; K. Burger, U. Wucherpfennig and E. Brunner, Adv. Heterocycl. Chem., 1994, 60, 1.
10. Biomedical Aspects of Fluorine Chemistry, ed. R. Filler and Y. Kobayashi, Elsevier, New York, 1992; J. M. Silvester, Aldrichim. Acta, 1991, 24, 31; M. J. Silvester, Adv. Heterocycl. Chem., 1994. 59, 1; K. Burger, U. Wucherpfennig and E. Brunner, Adv. Heterocycl. Chem., 1994, 60, 1.
11. Biomedical Aspects of Fluorine Chemistry, ed. R. Filler and Y. Kobayashi, Elsevier, New York, 1992; J. M. Silvester, Aldrichim. Acta, 1991, 24, 31; M. J. Silvester, Adv. Heterocycl. Chem., 1994. 59, 1; K. Burger, U. Wucherpfennig and E. Brunner, Adv. Heterocycl. Chem., 1994, 60, 1.
12. Biomedical Aspects of Fluorine Chemistry, ed. R. Filler and Y. Kobayashi, Elsevier, New York, 1992; J. M. Silvester, Aldrichim. Acta, 1991, 24, 31; M. J. Silvester, Adv. Heterocycl. Chem., 1994. 59, 1; K. Burger, U. Wucherpfennig and E. Brunner, Adv. Heterocycl. Chem., 1994, 60, 1.
13. P. Bravo and G. Resnati, Tetrahedron: Asymmetry, 1990, 1, 31; Fluorine in Bioorganic Chemistry, ed. J. T. Welch and S. Eswarakrishnan, Wiley, New York, 1991.
14. P. Bravo and G. Resnati, Tetrahedron: Asymmetry, 1990, 1, 31; Fluorine in Bioorganic Chemistry, ed. J. T. Welch and S. Eswarakrishnan, Wiley, New York, 1991.
15. P. Bravo, L. Bruché, A. Farina, I. I. Gerus, M. T. Kolytcheva, V. P. Kukhar, S. V. Meille and F. Viani, J. Chem. Soc., Perkin Trans. 1, 1995, 1667.
16. M. Christl and R. Huisgen, Chem. Ber., 1973, 106, 3291; P. Caramella, E. Albini, T. Bandiera, A. Corsico Coda, P. Grünanger, P. Vita Finzi and O. Vajna de Pava, J. Chem. Soc., Perkin Trans. 1, 1973, 1148; ,P. Bravo, L. Bruché, A. Mele and G. Zecchi, J. Chem. Res., 1991, (S) 81; (M) 0719.
17. M. Christl and R. Huisgen, Chem. Ber., 1973, 106, 3291; P. Caramella, E. Albini, T. Bandiera, A. Corsico Coda, P. Grünanger, P. Vita Finzi and O. Vajna de Pava, J. Chem. Soc., Perkin Trans. 1, 1973, 1148; ,P. Bravo, L. Bruché, A. Mele and G. Zecchi, J. Chem. Res., 1991, (S) 81; (M) 0719.
18. M. Christl and R. Huisgen, Chem. Ber., 1973, 106, 3291; P. Caramella, E. Albini, T. Bandiera, A. Corsico Coda, P. Grünanger, P. Vita Finzi and O. Vajna de Pava, J. Chem. Soc., Perkin Trans. 1, 1973, 1148; ,P. Bravo, L. Bruché, A. Mele and G. Zecchi, J. Chem. Res., 1991, (S) 81; (M) 0719.
19. M. Christl and R. Huisgen, Chem. Ber., 1973, 106, 3291; P. Caramella, E. Albini, T. Bandiera, A. Corsico Coda, P. Grünanger, P. Vita Finzi and O. Vajna de Pava, J. Chem. Soc., Perkin Trans. 1, 1973, 1148; ,P. Bravo, L. Bruché, A. Mele and G. Zecchi, J. Chem. Res., 1991, (S) 81; (M) 0719.
20. Ref. 1a, p. 340; ref. 1c, p. 31.
21. P. Bravo, L. Bruché, G. Fronza and A. Merli, Gazz. Chim. Ital., 1994, 124, 275.