Chiral capsules: Asymmetric binding in calixarene-based dimers

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12671-12672

  Castellano, Ronald K ^a,b   Kim, Byeang Hyean ^b,c   Rebek Jr , Julius ^b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001543691     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973132+     Document Type: Article

References (27)

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6. (a) Scheerder, J. The Complexation of Anions by Neutral Calixarenes Derivatives. Thesis, University of Twente, Enschede, The Netherlands, 1995.
7. (b) Scheerder, J.; Vreekamp, R. H.; Engbersen, J. F. J.; Verboom, W.; van Duynhoven, J. P. M.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 3476-3481.
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10. Although considerable attention has been focused on the synthesis of chiral monomeric calix[4]arenes, this work has yet to be extended to the generation of chiral capsules. For inherently chiral calix[4]arenes see: (a) Iwamoto, K.; Shimizu, H.; Araki, K.; Shinkai, S. J. Am. Chem. Soc. 1993, 115, 3997-4006.
11. (b) Ferguson, G.; Gallagher, J. F.; Giunta, L.; Neri, P.; Pappalardo, S.; Parisi, M. J. Org. Chem. 1994, 59, 42-53.
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15. (f) Böhmer, V. Liebigs Ann./Recueil 1997, 2019-2030 and references therein.
16. (g) Otsuka, H.; Shinkai, S. Supramol. Sci. 1997, 3, 189-205 and references therein.
17. For calix[4]arenes with chiral substituents see: (a) Arimura, T.; Kawabata, H.; Matsuda, T.; Muramatsu, T.; Satoh, H.; Fujio, K.; Manabe, O.; Shinkai, S. J. Org. Chem. 1991, 56, 301-306.
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20. (d) Neri, P.; Bottino, A.; Geraci, C.; Piattelli, M. Tetrahedron: Asymmetry 1996, 7, 17-20 and references therein.
21. 2,6]heptane.
22. 2 regions.
23. This type of phenomenon is analogous to the "carceroisomerism" previously observed in carceplexes: (a) Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204.
24. (b) Timmerman, P.; Verboom, W.; van Veggel, F. C. J. M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 2345-2348.
25. (c) Chapman, R. G.; Sherman, J. C. J. Am. Chem. Soc. 1995, 117, 9081-9082.
26. 3 (Δ;δ = 0.48).
27. βH coalesce, whereas Δδ between remaining split signals gradually decreases, e.g., Δδ between the methyl groups of the encapsulated guest decreases by 0.4 ppm.