Helical thiaza[2.2]metacyclophanes. Synthesis, structure, circular dichroism, absolute configuration

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1996, Pages 2937-2943

  Müller, Dirk ^a   Böhme, Marc ^a   Nieger, Martin ^a   Rissanen, Kari ^b   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748905900     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960002937     Document Type: Article

References (52)

1. F. Vögtle, Cyclophane Chemistry, Wiley, Chichester, 1993;
2. Cyclophan-Chemie, Teubner, Stuttgart, 1990;
3. J. Schulz and F. Vögtle, Top. Curr. Chem., 1994, 172, 41.
4. S. Grimme, S. D. Peyerimhoff, S. Bartram, F. Vögtle, A. Breest and J. Hormes, Chem. Phys. Lett., 1993, 213, 32.
5. B. Engels, S. Grimme, D. Worthman-Saleh, D. Müller and F. Vögtle, J. Chem. Soc., Perkin Trans. 2, 1995, 1185.
6. W. Tochtermann, U. Vagt and G. Snatzke, Chem. Ber., 1985, 118;
7. V. Buss and M. Klein, Chem. Ber., 1988, 121, 89;
8. K.-J. Przybilla, F. Vögtle, M. Nieger and S. Franken, Angew. Chem., 1988, 100, 987;
9. Int. Ed. Engl., 1988, 27, 976.
10. F. Vögtle, P. Knops and A. Ostrowicki, Chem. Ber., 1990, 132, 1859;
11. F. Vögtle, A. Ostrowicki, B. Begemann, M. Jansen, M. Nieger and E. Niecke, Chem. Ber., 1990, 123, 169;
12. P. Knops, P.-M. Windscheif, F. Vögtle, A. Roloff, M. Jansen, M. Nieger, E. Niecke and Y. Okamoto, Chem. Ber., 1991, 124, 1585;
13. F. Vögtle, A. Ostrowicki, P. Knops, S. Billen and K. Mittelbach, Pure Appl. Chem., 1990, 3, 505.
14. L. Ernst, V. Boekelheide and H. Hopf, J. Magn. Reson., 1993, 31, 669;
15. K. Nishiyama and T. Sugawara, Chem. Lett., 1992, 1409;
16. A. Tsuge, T. Ishii, S. Mataka and M. Tashiro, J. Chem. Res., 1992, (S) 312;
17. H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J. P. Desvergne and H. Bouas-Laurent, J. Chem. Soc., Chem. Commun., 1994, 1075;
18. B. König, S. Ramm, B. Knieriem, P. Bubenitschek, H. Hopf, P. G. Jones and A. de Meijere, Chem. Ber., 1994, 127, 2263;
19. G. J. Bodwell, R. Frim, H. Hopfand M. Rabinovitz, Chem. Ber., 1993, 126, 167;
20. L. Ernst, Liebigs Ann., 1995, 13.
21. F. Vögtle, R. Lemmerz and S. Grimme, Chem. Ber., 1994, 127, 2081;
22. S. Grimme, I. Pischel, F. Vögtle and M. Nieger, J. Am. Chem. Soc., 1995, 117, 157.
23. P. Knops, N. Sendhoff, H.-B. Mekelburger and F. Vögtle, Top. Curr. Chem., 1991, 168, 1.
24. A. Ostrowicki, E. Koepp and F. Vögtle, Top. Curr. Chem., 1992, 161, 37.
25. A. Ostrowicki and F. Vögtle, Synthesis, 1988, 1003.
26. (a) E. Kleinpeter, J. Hartmann, W. Schroth, O. Hofer and A. Kalchhauser, Monatsh. Chem., 1992, 123, 823;
27. (b) F. Vögtle, K.-J. Przybilla, A. Mannschreck, N. Pustet and P. Büllesbach, Chem. Ber., 1988, 121, 823.
28. K. Meurer, F. Vögtle, A. Mannschreck, G. Stühler, H. Puff and A. Roloff, J. Org. Chem., 1984, 49, 3485.
29. D. Müller, M. Nieger and F. Vögtle, J. Chem. Soc., Chem. Commun., 1994, 1361.
30. S. Raucher and P. Klein, Tetrahedron Lett., 1980, 21, 4061;
31. S. Scheibye, R. Shabana, S. O. Lawesson and C. Rommig, Tetrahedron Lett., 1982, 38, 993.
32. + force field optimised structures.
33. R. Hoss and F. Vögtle, Angew. Chem., 1994, 106, 389;
34. Int. Ed. Engl., 1994, 33, 375.
35. J. Zhang and J. S. Moore, J. Am. Chem. Soc., 1992, 114, 9701.
36. J. Schulz, M. Nieger and F. Vögtle, Chem. Ber., 1991, 124, 2797.
37. G. Bodwell, L. Ernst, M. W. Haenel and H. Hopf, Angew. Chem., 1989, 101, 509;
38. Int. Ed. Engl., 1989, 28, 455.
39. 2-protons is probably caused by complex motion of the aromatic rings, in which the two shown conformers are energetically favoured, as indicated by the calculations noted in ref. 15.
40. K. Rissanen, A. Ostrowicki and F. Vögtle, Act. Chem. Scand., 1990, 44, 268.
41. D. Enders, Alkylation of Chiral Hydrazones, in Asymmetric Synthesis, Academic Press, New York, 1984, vol. 3, p. 275;
42. D. Enders, K.-J. Heider and G. Raabe, Angew. Chem., 1993, 105, 592;
43. Int. Ed. Engl., 1993, 32, 598;
44. D. Enders, W. Bettray and H. Wahl, Angew. Chem., 1995, 107, 527;
45. Int. Ed. Engl., 1995, 34, 455.
46. T. Shibita, I. Okamoto and K. Ishii, J. Liquid Chromatogr., 1986, 9, 313;
47. A. Ichida and T. Shibita, in Chromatographic Chiral Separations, Marcel Dekker, New York, 1988, p. 218.
48. Y. Okamoto and K. Hatada, J. Liquid Chromatogr., 1986, 9, 369.
49. (a) N. Walker and D. Stuart, Acta Crystallogr., Sect. A, 1983, 39, 158;
50. (b) G. M. Sheldrick, in Crystallographic Computing, Oxford University Press, Oxford, 1985, vol. 3, p. 175;
51. (c) D. Watkin, B. Carruthers and P. W. Betteridge, CRYSTALS, Chemical Crystallography Laboratory, Oxford, England, 1990.
52. SHELXTL-PLUS, G. M. Sheldrick, Siemens Analytical X-ray Instruments Incorporation, Madison, WI, US, 1989.