N-Methyl- and N-benzyl-4-amino[2.2]paracyclophanes as unique planar chiral auxiliaries

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 21, 1997, Pages 3137-3139

  Pelter, Andrew ^a   Kidwell, Huw ^a   Crump, Roger A N C ^a  

^a SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748829816     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705449a     Document Type: Article

References (31)

1. F. Vögtle, Cyclophane Chemistry, J. Wiley and Sons, New York, 1993.
2. H. Hope, J. Bernstein and K. N. Trueblood, Acta Crystallogr., Sect. B, 1972, 28, 1733.
3. D. J. Cram, R. B. Hornby, E. A. Truesdale, H. J. Reich, M. M. Delton and J. M. Cram, Tetrahedron, 1974, 30, 1757.
4. (a) F. Vögtle and P. Neumann, Synthesis, 1973, 85;
5. (b) F. Vögtle, Top. Curr. Chem., 1974, 48, 67;
6. (c) V. Bockelheide, Top. Curr. Chem., 1983, 113, 89;
7. (d) J. Kleinschroth and H. Hopf, Angew. Chem., Int. Ed. Engl., 1982, 21, 469;
8. (e) Cyclophanes, ed. P. M. Keehn and S. M. Rosenfeld, Academic Press, New York, vols. 1 and 2, 1983.
9. M. Brink, Synthesis, 1975, 807;
10. M. L. Kaplan and E. A. Truesdale, Tetrahedron Lett., 1976, 3665;
11. S. H. El Tamany and H. Hopf, Tetrahedron Lett., 1980, 21, 4901;
12. H. Hopf, I. Boehm and J. Kleinschroth, Org. Synth., 1981, 60, 41;
13. G. Bornenge, A. Malacride, S. Compolini and M. A. Beretta, Eur. Pat. Appl., 1987, 252 402; Ind. Eng. Chem. Res., 1989, 28, 1125;
14. R. Ungarelli, M. A. Beretta and L. Sogli, Eur. Pat. Appl., 1988, 307 934.
15. H. J. Reich and D. J. Cram, J. Am. Chem. Soc., 1969, 91, 3517.
16. R. Yanada, M. Higashikawa, Y. Miwa, T. Taga and F. Yoneda, Tetrahedron Lett., 1992, 3, 1387.
17. H. J. Reich and K. E. Yelm, J. Org. Chem., 1991, 56, 5672.
18. D. Y. Antonov, Y. N. Belekon, N. S. Ikonnikov, S. A. Orova, A. P. Pisarevsky, N. I. Raevski, V. I. Rozenberg, E. V. Sergeeva, Y. T. Struchkov, V. I. Tararov and E. V. Vorontsov, J. Chem. Soc., Perkin Trans. 1, 1995, 1873.
19. E. V. Sergeeva, V. I. Rozenberg, E. V. Vorontzov, T. I. Danilova, Z. A. Starikova, A. I. Yanovsky and Y. N. Belekon, Tetrahedron: Asymmetry, 1996, 7, 3445.
20. A. Pelter, R. A. N. C. Crump and H. Kidwell, Tetrahedron Lett., 1996, 37, 1273.
21. D. J. Cram, W. J. Wechter and R. W. Kierstead, J. Am. Chem. Soc., 1958, 80, 3126;
22. J. L. Marshall and L. Hall, Tetrahedron, 1981, 37, 1271.
23. H. Falk, P. Reich-Rohrwig and K. Schlögl, Tetrahedron, 1970, 26, 511;
24. N. Nakazaki, K. Yamamoto and M. Maeda, Chem. Lett., 1980, 1553;
25. W. Tochtermann, G. Olsson, C. Vogt, K. Peters and H. G. von Schnering, Chem. Ber., 1987, 120, 1523;
26. A. Pelter, H. Kidwell and D. Hibbs, unpublished X-ray analysis of R-(-)-13-bromo-4-methoxycarbonyl[2.2]paracyclophane.
27. A. Cipiciani, F. Fringuelli, V. Mancini, O. Piermatti, F. Pizzo and R. Ruzzicorni, J. Org. Chem., 1997, 62, 3744.
28. R. S. Ward, A. Pelter, D. Goubet and M. C. Pritchard, Tetrahedron: Asymmetry, 1995, 6, 469.
29. K. Koh and T. Durst, Tetrahedron Lett., 1993, 34, 4473.
30. We thank Dr D. Hibbs, EPSRC X-ray crystallography centre, Cardiff, for this analysis.
31. R. S. Cahn, C. Ingold and V. Prelog, Angew. Chem., Int. Ed. Engl., 1966, 5, 385.