Chiral β-amino sulfoxides. Synthesis, configurational assignment and conformational analysis based on X-ray, CD, 1H NMR and theoretical calculations

Tetrahedron

Volumn 54, Issue 23, 1998, Pages 6571-6586

  Lewanowicz, A ^a   Lipinski J ^a   Siedlecka, R ^a   Skarzewski, J ^a   Baert, F ^b  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b UNIV LILLE   (France)

Author keywords

Amino sulfoxides; CD spectra; Conformational analysis; X ray structure

Indexed keywords

SULFOXIDE;

ARTICLE; CIRCULAR DICHROISM; DRUG CONFORMATION; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0032482293     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00317-2     Document Type: Article

References (33)

1. 1. Carreno, C. M. Chem. Rev., 1995, 95, 1717.
2. 2. Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett., 1988, 29, 6101; Ruano, J. L. G.; Lorente, A.; Rodriguez, J. H. Tetrahedron Lett., 1992, 33, 5637; Pyne, S. G.; Hajipour, A. R. Tetrahedron, 1994, 50, 13501; Bravo, P.; Crucianelli, M.; Zanda, M. Tetrahedron Lett., 1995, 36, 3043.
3. 2. Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett., 1988, 29, 6101; Ruano, J. L. G.; Lorente, A.; Rodriguez, J. H. Tetrahedron Lett., 1992, 33, 5637; Pyne, S. G.; Hajipour, A. R. Tetrahedron, 1994, 50, 13501; Bravo, P.; Crucianelli, M.; Zanda, M. Tetrahedron Lett., 1995, 36, 3043.
4. 2. Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett., 1988, 29, 6101; Ruano, J. L. G.; Lorente, A.; Rodriguez, J. H. Tetrahedron Lett., 1992, 33, 5637; Pyne, S. G.; Hajipour, A. R. Tetrahedron, 1994, 50, 13501; Bravo, P.; Crucianelli, M.; Zanda, M. Tetrahedron Lett., 1995, 36, 3043.
5. 2. Ronan, B.; Marchalin, S.; Samuel, O.; Kagan, H. B. Tetrahedron Lett., 1988, 29, 6101; Ruano, J. L. G.; Lorente, A.; Rodriguez, J. H. Tetrahedron Lett., 1992, 33, 5637; Pyne, S. G.; Hajipour, A. R. Tetrahedron, 1994, 50, 13501; Bravo, P.; Crucianelli, M.; Zanda, M. Tetrahedron Lett., 1995, 36, 3043.
6. 3. For preliminary communication, see: Siedlecka, R.; Skarzewski, J. Synlett, 1996, 757.
7. 4. Solladie, G.; Greek, C.; Demailly, G.; Solladie-Cavallo, A. Tetrahedron Lett., 1982, 23, 50437; Solladie, G.; Frechau, C.; Demailly, G.; Greek, C. J. Org. Chem., 1985, 50, 1552; Carreno, M. C.; Ruano, J. L. G.; Martin, A. M.; Pedregal, C.; Rodriguez, J. H.; Rubia, A.; Sanchez, J., Solladie, G. J. Org. Chem., 1990, 55, 2120; Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Meille, S. V.; Zanda, M. J. Org. Chem., 1996, 61, 3375.
8. 4. Solladie, G.; Greek, C.; Demailly, G.; Solladie-Cavallo, A. Tetrahedron Lett., 1982, 23, 50437; Solladie, G.; Frechau, C.; Demailly, G.; Greek, C. J. Org. Chem., 1985, 50, 1552; Carreno, M. C.; Ruano, J. L. G.; Martin, A. M.; Pedregal, C.; Rodriguez, J. H.; Rubia, A.; Sanchez, J., Solladie, G. J. Org. Chem., 1990, 55, 2120; Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Meille, S. V.; Zanda, M. J. Org. Chem., 1996, 61, 3375.
9. 4. Solladie, G.; Greek, C.; Demailly, G.; Solladie-Cavallo, A. Tetrahedron Lett., 1982, 23, 50437; Solladie, G.; Frechau, C.; Demailly, G.; Greek, C. J. Org. Chem., 1985, 50, 1552; Carreno, M. C.; Ruano, J. L. G.; Martin, A. M.; Pedregal, C.; Rodriguez, J. H.; Rubia, A.; Sanchez, J., Solladie, G. J. Org. Chem., 1990, 55, 2120; Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Meille, S. V.; Zanda, M. J. Org. Chem., 1996, 61, 3375.
10. 4. Solladie, G.; Greek, C.; Demailly, G.; Solladie-Cavallo, A. Tetrahedron Lett., 1982, 23, 50437; Solladie, G.; Frechau, C.; Demailly, G.; Greek, C. J. Org. Chem., 1985, 50, 1552; Carreno, M. C.; Ruano, J. L. G.; Martin, A. M.; Pedregal, C.; Rodriguez, J. H.; Rubia, A.; Sanchez, J., Solladie, G. J. Org. Chem., 1990, 55, 2120; Arnone, A.; Bravo, P.; Capelli, S.; Fronza, G.; Meille, S. V.; Zanda, M. J. Org. Chem., 1996, 61, 3375.
11. 5. Brunet, E.; Gallego, M. T.; Ruano, J. L. G.; Alcudia, P. Tetrahedron, 1986, 42, 423.
12. 6. Alvarez-Ibara, C.; Cuervo-Rodriguez, R.; Fernandez-Montreal, M. C.; Ruiz, M. P. J. Org. Chem., 1994, 59, 7284.
13. 7. Lewanowicz, A.; Roszak, S.; Siedlecka, R. Mol. Phys. Reports 1996, 16, 9.
14. 8. Nakagawa, I.; Hata, T. Tetrahedron Lett., 1975, 1409; Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1, 1983, 1315; Kotsuki, H.; Matsumoto, K.; Nishizawa, H. Tetrahedron Lett., 1991, 32, 4155.
15. 8. Nakagawa, I.; Hata, T. Tetrahedron Lett., 1975, 1409; Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1, 1983, 1315; Kotsuki, H.; Matsumoto, K.; Nishizawa, H. Tetrahedron Lett., 1991, 32, 4155.
16. 8. Nakagawa, I.; Hata, T. Tetrahedron Lett., 1975, 1409; Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1, 1983, 1315; Kotsuki, H.; Matsumoto, K.; Nishizawa, H. Tetrahedron Lett., 1991, 32, 4155.
17. 9. Cran, G. A.; Gibson, C. L.; Handa, S. Tetrahedron Asymmetry 1995, 6, 1553.
18. 10. Hoogwater, D. A.; Reinhoudt, D. N.; Lie, T. S.; Gunnenweg, J. J.; Beyerman, H. C.; Recueil 1973, 92, 819.
19. 11. Mislow, K.; Green, M. M.; Laur, P.; Melillo, J. T.; Simmons, T.; Ternay, A. L. J. Am. Chem. Soc., 1965, 87, 1958.
20. 12. Jones, D. N.; Green, M. J. C. Chem. Soc. (C), 1967, 532.
21. 13. Kaźmierczak, F.; Gawrońska, K.; Rychlewska, U.; Gawroński, J. Tetrahedron: Asymmetry 1994, 5, 527 and references cited therein.
22. 14. Sheldrick, G. M. (1985). SHELXS86. Program for the Solution of Crystal Structures. University of Göttingen, Germany.
23. 15. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc., 1977, 99, 4899.
24. 16. Karplus, M. J. Chem. Phys., 1959, 30, 11;
25. Karplus, M. J. Am. Chem. Soc., 1963, 85, 2870.
26. 17. Acton, N.; Komoriya, A. Org. Prep. Proc. Int., 1982, 14, 381.
27. 18. Koga, K.; Matsuo, H.; Yamada, S. Chem. Pharm. Bull., 1966, 14, 243.
28. 19. Iwakura, Y.; Hayashi, K.; Iwata, K. Macromol. Chem., 1967, 704, 46.
29. 20. O'Brien, P. M.; Sliskovic, D. R.; Blankley, C. J.; Roth, B. D.; Wilson, M. W.; Hamelehle, K. L.; Krauze, B. R.; Stanfield, R. L. J. Med. Chem., 1994, 37, 1810.
30. 21. Reihlen, H.; Knopfle, L.; Sapper, W. Liebigs Ann. Chem; 1938, 543, 247.
31. 22. Furukawa, N.; Yoshimura, T.; Ohtsu, M.; Akasaka, T.; Oae, S. Tetrahedron, 1980, 36, 73.
32. 23. Bates, R. B.; Janda, K. D. Synthesis, 1984, 310.
33. 24. Kano, S.; Yokomatsu, T.; Shibuya, S. J. Org. Chem., 1989, 54, 513.