Asymmetric 1,3-Dipolar Cycloadditions of Nitrile Oxides and Nitrones with Fluorosubstituted Chiral Vinyl Sulfoxides

Journal of Chemical Research - Part S

Volumn , Issue 8, 1996, Pages 348-349

  Bravo, Pierfrancesco ^a   Bruché, Luca ^a   Crucianelli, Marcello ^b   Farina, Alessandra ^a   Meille, Stefano Valdo ^a   Merli, Annamaria ^a   Seresini, Paolo ^a  

^a POLITECNICO DI MILANO   (Italy)

^b UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742594847     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984; W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990.
2. 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984; W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, 1990.
3. (a) K. B. G. Torssell, Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, VCH, New York, 1988, p. 25;
4. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
5. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
6. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
7. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
8. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
9. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
10. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
11. (b) R. Annunziata, M. Cinquini, F. Cozzi and L. Raimondi, Gazz. Chim. Ital., 1989, 119, 253 and references cited therein; T. Olsson, K. Stern, G. Westman and S. Sundell, Tetrahedron, 1990, 46, 2473 and references cited therein; A. J. Stack, T. A. Heffner, S. J. Geib and D. P. Curran, Tetrahedron, 1993, 49, 995 and references cited therein; A. N. Boa, D. A. Dawkins, A. R. Hergueta and P. R. Jenkins, J. Chem. Soc., Perkin Trans. 1, 1994, 953; M. T. Rispens, E. Keller, B. de Lange, R. W. J. Zijlstra and B. L. Feringa, Tetrahedron: Asymmetry, 1994, 5, 607; H. Waldmann, E. Blaser, M. Jansen and H. P. Letschert, Angew. Chem., Int. Ed. Engl., 1995, 34, 150; G. B. Jones and B. J. Chapman, Synthesis, 1995, 475; D. M. Cooper, R. Grigg, S. Hargreaves, P. Kennewell and J. Redpath, Tetrahedron, 1995, 51, 7791 and references cited therein.
12. G. H. Posner, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, p. 225; G. H. Posner, in The Chemistry of Sulphoxides and Sulphones, eds. S. Patai, Z. Rappoport and C. J. M. Stirling, Wiley, New York, 1988, ch. 16.
13. G. H. Posner, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, p. 225; G. H. Posner, in The Chemistry of Sulphoxides and Sulphones, eds. S. Patai, Z. Rappoport and C. J. M. Stirling, Wiley, New York, 1988, ch. 16.
14. (a) T. Koizumi, H. Hirai and E. Yoshii, J. Org. Chem., 1982, 47, 4004;
15. (b) T. Takahashi, A. Fujii, J. Sugita, T. Hagi, K. Kitano, Y. Arai, T. Koizumi and M. Shiro, Tetrahedron: Asymmetry, 1991, 2, 1379.
16. (a) P. Bravo and G. Resnati, Tetrahedron: Asymmetry, 1990, 1, 31;
17. (b) P. Bravo, A. Farina, M. Frigerio, S. V. Meille and F. Viani, Tetrahedron: Asymmetry, 1994, 5, 987 and references cited therein.
18. Ref. 2(a), p. 14.
19. P. Bravo, L. Bruché, G. Fronza and A. Merli, Gazz. Chim. Ital., 1994, 124, 275.
20. P. Bravo, L. Bruché, A. Farina, G. Fronza, S. V. Meille and A. Merli, Tetrahedron: Asymmetry, 1993, 4, 2131.
21. P. Bravo, L. Bruché, M. Crucianelli and A. Merli, J. Fluorine Chem., 1995, 74, 127.
22. (a) 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;
23. (a) 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;
24. (b) P. Bravo, L. Bruché, A. Mele and G. Zecchi, J. Chem. Res., 1991, (S) 81, (M) 719.
25. (b) P. Bravo, L. Bruché, A. Mele and G. Zecchi, J. Chem. Res., 1991, (S) 81, (M) 719.
26. H. D. Flack, Acta Crystallogr., Sect. A, 1983, 39, 876.
27. F. M. Allen, O. Kennard, D. G. Watson, L. Btammer, A. G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1-S19.
28. A. Altomare, G. Cascarano, G. Giacovazzo and A. Guagliardi, J. Appl. Crystallogr., 1993, 26, 343.
29. G.M. Sheldrick, SHELXL93, Program for Structure Refinement, University of Gottingen, Germany, 1993.