Chiral dendrophanes, dendro[2]rotaxanes, and dendro[2]catenanes: Synthesis and chiroptical phenomena

European Journal of Organic Chemistry

Volumn , Issue 17, 2000, Pages 3059-3067

  Reuter, Carin ^a   Pawlitzki, Gregor ^a   Wörsdörfer, Udo ^a   Plevoets, Marcus ^a   Mohry, André ^a   Kubota, Takateru ^b   Okamoto, Yoshio ^b   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

Catenanes; Chirality; Cyclophanes; Dendrimers; Rotaxanes

Indexed keywords

CATENANE; CYCLOPHANE; DENDRIMER; DENDROPHANE; DENDRO[2]CATENANE; DENDRO[2]ROTAXANE; MACROCYCLIC COMPOUND; PARACYCLOPHANE DERIVATIVE; ROTAXANE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; RACEMIC MIXTURE; SYNTHESIS;

EID: 0033816664     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200009)2000:17<3059::AID-EJOC3059>3.0.CO;2-T     Document Type: Article

References (68)

1. [1a] G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules, Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996.
2. [1b] D. A. Tomalia, A. M. Naylor, W. A. Goddart III, Angew. Chem. 1990, 102, 119-157; Angew. Chem. Int. Ed. Engl. 1990, 29, 113-151.
3. [1b] D. A. Tomalia, A. M. Naylor, W. A. Goddart III, Angew. Chem. 1990, 102, 119-157; Angew. Chem. Int. Ed. Engl. 1990, 29, 113-151.
4. [1c] G. R. Newkome, C. N. Moorefield, G. R. Baker, A. L. Johnson, R. K. Behera, J. Org. Chem. 1992, 57, 358-362.
5. [1d] K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1991, 113, 4252-4261.
6. [1e] K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, Angew. Chem. 1994, 106, 123-126; Angew. Chem. Int. Ed. Engl. 1994, 33, 82-85.
7. [1e] K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, Angew. Chem. 1994, 106, 123-126; Angew. Chem. Int. Ed. Engl. 1994, 33, 82-85.
8. [1f] M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955; Angew. Chem. Int. Ed. 1999, 38, 884-905.
9. [1f] M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955; Angew. Chem. Int. Ed. 1999, 38, 884-905.
10. [1g] P. K. Murer, J.-M. Lapierre, G. Greiveldinger, D. Seebach, Helv. Chim. Acta 1997, 80, 1648-1681.
11. [1h] D. Seebach, P. B. Rheiner, G. Greiveldinger, T. Butz, H. Sellner, Top. Curr. Chem. 1998, 197, 125-164.
12. [1i] H. Sellner, D. Seebach, Angew. Chem. 1999, 111, 2039-2041; Angew. Chem. Int. Ed. 1999, 38, 1918-1920.
13. [1i] H. Sellner, D. Seebach, Angew. Chem. 1999, 111, 2039-2041; Angew. Chem. Int. Ed. 1999, 38, 1918-1920.
14. [1j] R. G. Denkewalter, J. F. Kole, W. J. Lukasavage, US Pat. 4,289,872 1981.
15. [1k] R. G. Denkewalter, J. F. Kole, W. J. Lukasavage, US Pat. 4,360,646 1982.
16. [1l] R. G. Denkewalter, J. F. Kole, W. J. Lukasavage, US Pat. 4,410,688 1983.
17. [1m] H.W.I. Peerlings, E. W. Meijer, Chem. Eur. J. 1997, 3, 1563-1570.
18. [1n] C. W. Thomas, Y. Tor, Chirality 1998, 10, 53-59.
19. [1o] J. F. G. A. Jansen, H. W. I. Peerlings, E. M. M. de Brabander-Van den Berg, E. W. Meijer, Angew. Chem. 1995, 107, 1321-1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1206-1209.
20. [1o] J. F. G. A. Jansen, H. W. I. Peerlings, E. M. M. de Brabander-Van den Berg, E. W. Meijer, Angew. Chem. 1995, 107, 1321-1324; Angew. Chem. Int. Ed. Engl. 1995, 34, 1206-1209.
21. [1p] J. R. McElhanon, D. V. McGrath, J. Am. Chem. Soc. 1998, 120, 1647-1656.
22. [1q] D. M. Junge, D. V. McGrath, Tetrahedron Lett. 1998, 39, 1701-1704.
23. [1r] A. Ritzen, T. Frejd, Chem. Commun. 1999, 207-208.
24. [1s] U. Lüning, Nachr. Chem. Techn. Lab. 2000, 48, 134-137,
25. [1t] S. Bodige, A. S. Torres, D. J. Maloney, D. Tate, G. R. Kinsel, A. K. Walker, F. M. MacDonnell, J. Am. Chem. Soc. 1997, 119, 10364-10369.
26. [2a] S. Yamango, M. Furukawa, A. Azuma, J.-I. Yoshida, Tetrahedron Lett. 1998, 39, 3783-3786.
27. [2b] H.-F. Chow, C. C. Mak, J. Org. Chem. 1997, 62, 5116-5127.
28. [2c] C. Bolm, N. Derrien, A. Seger, Synlett 1996, 387-388.
29. [2d] P. B. Rheiner, P. Murer, D. Seebach, Chimia 1996, 50, 352.
30. [2e] H. Brunner, J. Organomet. Chem. 1995, 500, 39-46.
31. [2f] H. Brunner, S. Altman, Chem. Ber. 1994, 127, 2285-2296.
32. [2g] H. Brunner, I. Poleschak, Z. Naturforsch. Teil B 1997, 52, 839-846.
33. [2h] C. Bolm, N. Derrien, A. Seger, Chem. Commun. 1999, 2087-2088.
34. [2i] R. Schneider, C. Köllner, I. Weber, A. Togni, Chem. Commun. 1999, 2415-2416.
35. [2j] M.-J. Wu, U. Chaudhry, D. V. McGrath, Tetrahedron Lett. 1996, 37, 6077-6080.
36. [2k] P. Murer, D. Seebach, Angew. Chem. 1995, 107, 2297-2300; Angew. Chem. Int. Ed. Engl. 1995, 34, 2116-2119.
37. [2k] P. Murer, D. Seebach, Angew. Chem. 1995, 107, 2297-2300; Angew. Chem. Int. Ed. Engl. 1995, 34, 2116-2119.
38. [2l] M. S. T. H. Sanders-Hovens, J. F. G. A. Jansen, J. A. J. M. Vekemans, E. W. Meijer, Polym. Mater. Sci. Eng. 1995, 73, 338-339.
39. [3a] H. Wynberg, G. L. Hekkert, J. P. M. Houbiers, H. W. Bosch, J. Am. Chem. Soc. 1965, 87, 2635-2639.
40. [3b] H. Wynberg, L. A. Hulshof, Tetrahedron 1974, 30, 1775-1782.
41. [3c] W. Ten Hoeve, H. Wynberg, J. Org. Chem 1980, 45, 2754-2763.
42. [3d] W. A. Sanderson, H. S. Mosher, J. Am. Chem. Soc. 1966, 88, 4185-4190.
43. [3e] H. O. L. Fischer, E. Bear, Chem. Rev. 1941, 29, 287.
44. [3f] K. Mislow, R. Graeve, A. J. Gordon, G. H. Wahl, Jr., J. Am. Chem. Soc. 1964, 86, 1733-1741.
45. See reference [2a], and H. W Peerlings, E. W. Meijer, Eur. J. Org. Chem. 1998, 573-577.
46. J. Issberner, M. Böhme, S. Grimme, M. Nieger, W. Paulus, F. Vögtle, Tetrahedron: Asymmetry 1996, 7, 2223-2232.
47. K. Mislow, P. Bickart, Isr. J. Chem. 1977, 15, 1-6.
48. [7a] H. W. Peerlings, M. P. Struijk, E. W. Meijer, Chirality 1998, 10, 46-52.
49. [7b] H. W. Peerlings, D. C. Trimbach, E. W. Meijer, Chem. Commun. 1998, 497-498.
50. For the definition of planar-chirality see: [8a] K. Schlögl, Top. Curr. Chem. 1984, 125, 27-62.
51. [8b] E. L. Eliel, S. H. Wilen, Organische Stereochemie (Eds.: H. Hopf, J. Mulzer), Wiley-VCH, Weinheim, 1998.
52. [8c] S. Grimme, J. Harren, A. Sobanski, F. Vögtle, Eur. J. Org. Chem. 1998, 1491-1509.
53. For the definition of cyclo-chirality and topological chirality see: [9a] W. Closson in H. L. Frisch, E. Wasserman, J. Am. Chem. Soc. 1961, 83, 3789-3795.
54. [9b] V. Prelog, H. Gerlach, Helv. Chim. Acta 1964, 47, 2288-2294.
55. [9c] H. Gerlach, J. A. Owtschinnikow, Helv. Chim. Acta 1964, 47, 2294-2304
56. [9d] R. Cruse in: Stereochemie der Kohlenstoffverbindungen (Ed.: E. L. Eliel), Verlag Chemie, Weinheim, Germany, 1966, 215-225.
57. [9e] M. Chorev, M. Goodman, Acc. Chem. Res. 1979, 12, 1-7.
58. [9f] C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 10547-10548.
59. [9g] A. Mohry, M. Nieger, F. Vögtle, Chirality 2000, 12, 76-83.
60. All side products of the substitution reaction were analysed by FAB-or MALDI-TOF mass spectrometry but otherwise not fully characterised.
61. [11a] E. Yashima, Y. Okamoto, Bull. Chem. Soc. Jpn. 1995, 68, 3289-3307.
62. [11b] For a review, see: Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1073-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043.
63. [11b] For a review, see: Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1073-1095; Angew. Chem. Int. Ed. 1998, 37, 1020-1043.
64. π→π* Transfer of the [2.2]paracyclophane core.
65. [13a] H. J. Reich, D. J. Cram, J. Am. Chem. Soc. 1969, 91, 3534-3543.
66. [13b] D. J. Cram, M. I. Allinger, J. Am. Chem. Soc. 1955, 77, 6289-6294.
67. R. Jäger, M. Händel, J. Harren, K. Rissanen, F. Vögtle, Liebigs Ann. 1996, 1201-1207.
68. S. Ottens-Hildebrandt, T. Schmidt, J. Harren, F. Vögtle, Liebigs Ann. 1995, 1855-1860.