Dendrimers with inherently axially chiral units

Journal of Materials Chemistry

Volumn 10, Issue 5, 2000, Pages 1061-1073

  Lellek, Vít ^a   Stibor, Ivan ^b  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

DENDRIMER; OLIGOMER;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; DIASTEREOISOMER; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; SYNTHESIS;

EID: 0034027777     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907825h     Document Type: Article

References (47)

1. 1 R. G. Denkewalter, J. Kolc and W. J. Lukasavage, Allied Corp., USA Pat. 4.289 872, 1981 (Chem. Abstr., 1985, 102, P79324q).
2. 2 G. R. Newkome, C. N. Moorfield and F. Vögtle, Dendritic Molecules: Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996, pp. 183-200.
3. 3 H. W. I. Peerlings and E. W. Meijer, Chem. Eur. J., 1997, 3, 1563.
4. 4 (a) A. Archut and F. Vögtle, Chem. Soc. Rev., 1998, 27, 233;
5. (b) D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353;
6. (c) M. A. Hearshaw and J. R. Moss, Chem. Commun., 1999, 1;
7. (d) M. Fischer and F. Vögtle, Angew. Chem., Int. Ed., 1999, 38, 884.
8. 5 H.-T. Chang, Ch.-T. Chen, T. Kondo, G. Siuzdak and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1996, 35, 182.
9. 6 J. R. McElhanon and D. V. McGrath, J. Am. Chem. Soc., 1998, 120, 1647.
10. 7 (a) D. Zanini and R. Roy, J. Am. Chem. Soc., 1997, 119, 2088;
11. (b) H. C. Hansen, S. Haataja, J. Finne and G. Magnusson, J. Am. Chem. Soc., 1997, 119, 6974;
12. (c) J. Kadokawa, M. Sato, M. Karasu, H. Tagaya and K. Chiba, Angew. Chem., Int. Ed., 1998, 37, 2373;
13. (d) R. Roy and J. M. Kim, Angew. Chem., Int. Ed., 1999, 38, 369.
14. 8 (a) L. Zhang and J. P. Tam, J. Am. Chem. Soc., 1997, 119, 2363;
15. (b) H.-F. Chow, K.-K. Mong, M. F. Nongrum and C. W. Wan, Tetrahedron, 1998, 54, 8543;
16. (c) A. Ritzén and T. Frejd, Chem. Commun., 1999, 207.
17. 9 (a) P. K. Murer and D. Seebach, Polym. Mater. Sci. Eng., 1997, 77, 69;
18. (b) P. Murer and D. Seebach, Helv. Chim. Acta, 1998, 81, 603;
19. (c) G. Greiveldinger and D. Seebach, Helv. Chim. Acta, 1998, 81, 1003.
20. 10 S. Yamago, M. Furukawa, A. Azuma and J.-I. Yoshida, Tetrahedron Lett., 1998, 39, 3783.
21. 11 (a) H. W. I. Peerlings and E. W. Meijer, Eur. J. Org. Chem., 1998, 573;
22. (b) Y.-M. Chen, Ch.-F. Chen and F. Xi, Chirality, 1998, 10, 661.
23. 12 (a) C. Rosini, L. Franzini, A. Raffaelli and P. Salvadori, Synthesis, 1992, 503;
24. (b) L. Pu, Chem. Rev., 1998, 98, 2405.
25. 13 (a) H. Sellner and D. Seebach, Angew. Chem., Int. Ed., 1999, 38, 1918;
26. (b) A. Schmitzer, E. Perez, I. Rico-Lattes and A. Lattes, Tetrahedron Lett., 1999, 40, 2947.
27. 14 V. Lellek and I. Stibor, Collect. Czech. Chem. Commun., 1997, 62, 925.
28. 15 G. Mann, H. Wilde and J. Lehmann, J. Prakt. Chem., 1978, 320, 715.
29. 16 G. R. Newkome and X. Lin, Macromolecules, 1991, 24, 1443.
30. 17 H.-F. Chow and C. C. Mak, Pure Appl. Chem., 1997, 69, 483.
31. 18 (a) B. Suchod, A. Renault, J. Lajzerovicz and G. P. Spada, J. Chem. Soc., Perkin Trans. 2, 1992, 1839;
32. (b) S. Pakhomova, B. Kratochvíl, V. Lellek and I. Stibor, Acta Crystallogr., Sect. C, 1997, 53, 1871.
33. 19 The described phenomenon is typical not only for these amides. Many 3'-alkyl substituted 2,2'-dimethoxy-1,1'-binaphthalene-3-carboxylates also show this effect. See V. Lellek, PhD Thesis, Prague Institute of Chemical Technology, Prague, 1997.
34. 20 The bathochromic shifted weak maximum at 256 nm is also typical for many 3'-and 6'-alkyl substituted 2,2'-dimethoxy-1,1'-binaphthalene-3-carboxylates, see V. Lellek, PhD Thesis.
35. 21 J. J. G. S. van Es, H. A. M. Biemans and E. W. Meijer, Tetrahedron: Asymmetry, 1997, 8, 1825 and references cited herein.
36. 22 (a) Stereoselective Synthesis in Methods of Organic Chemistry (Houben-Weyl) E 21, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, Georg Thieme Verlag, Stutgart, 1996;
37. (b) R. Noyori, in Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, New York, 1994.
38. 23 (a) P. Weyermann, J.-P. Gisselbrecht, C. Boudon, F. Diederich and M. Gross, Angew. Chem., 1999, 111, 3400;
39. (b) P. B. Rheiner and D. Seebach, Chem. Eur. J., 1999, 5, 3221;
40. (c) C. B. Gorman, J. C. Smith, M. W. Hager, B. L. Parkhurst, H. Sierputowska-Gracz and C. A. Haney, J. Am. Chem. Soc., 1999, 121, 9958;
41. (d) M. E. Piotti, F. Rivera Jr., R. Bond, C. J. Hawker and J. M. J. Fréchet, J. Am. Chem. Soc., 1999, 121, 9471;
42. (e) C. Bolm, N. Derrien and A. Seger, Chem. Commun., 1999, 2087.
43. 24 (a) G. R. Newkome, E. He and C. N. Moorefield, Chem. Rev., 1999, 99, 1689;
44. (b) Y. Wang, C. M. Cardona and A. E. Kaifer, J. Am. Chem. Soc., 1999, 121, 9756;
45. (c) D. J. Diaz, G. D. Storrier, S. Bernhard, K. Takada and H. D. Abruna, Langmuir, 1999, 15, 7351;
46. (d) M. Plevoets, F. Vögtle, L. De Cola and V. Balzani, New J. Chem., 1999, 63.
47. 25 D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta, 1999, 82, 1225.