Synthesis and optical resolution of naphthalene-containing inherently chiral calix[4]arenes derived by intramolecular ring closure or stapling of proximal phenyl units

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1996, Pages 1945-1950

  Ikeda, Atsushi ^a   Yoshimura, Makoto ^a   Lhotak, Pavel ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748905328     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001945     Document Type: Article

References (29)

1. C. D. Gutsche, Calixarenes, Royal Society of Chemistry, Cambridge, 1989;
2. Calixarenes - A Versatile Class of Macrocyclic Compounds, ed. J. Vicens and V. Böhmer, Kluwer Academic Press, Dordrecht, 1991.
3. S. Shinkai, Tetrahedron, 1993, 49, 8933;
4. V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
5. Very recently, the first successful example for chiral recognition of primary ammonium guests has been demonstrated by using an inherently chiral homooxacalix[3]arene derivative: K. Araki, K. Inada and S. Shinkai, Angew. Chem., Int. Ed. Engl., 1996, 35, 72.
6. R. Muthukrishnan and C. D. Gutsche, J. Org. Chem., 1979, 44, 3962.
7. S. Shinkai, T. Arimura, H. Satoh and O. Manabe, J. Chem. Soc., Chem. Commun., 1987, 1495;
8. T. Arimura, S. Edamitsu, S. Shinkai, O. Manabe, T. Muramatsu and M. Tashiro, Chem. Lett., 1987, 2269.
9. T. Arimura, H. Kawabata, T. Matsuda, T. Muramatsu, H. Satoh, K. Fujio, O. Manabe and S. Shinkai, J. Org. Chem., 1991, 56, 301.
10. A. Ikeda, T. Nagasaki and S. Shinkai, J. Phys. Org. Chem., 1992, 5, 699.
11. K. Iwamoto, A. Yanagi, T. Arimura, T. Matsuda and S. Shinkai, Chem. Lett., 1990, 1901;
12. K. Iwamoto, H. Shimizu, K. Araki and S. Shinkai, J. Am. Chem. Soc., 1993, 115, 3997.
13. S. Pappalardo, S. Caccamese and L. Giunta, Tetrahedron Lett., 1991, 32, 7747.
14. S. Shinkai, T. Arimura, H. Kawabata, H. Murakami, K. Araki, K. Iwamoto and S. Shinkai, J. Chem. Soc., Chem. Commun., 1990, 1734;
15. S. Shinkai, T. Arimura, H. Kawabata, H. Murakami and K. Iwamoto, J. Chem. Soc., Perkin Trans. 1, 1991, 2429;
16. V. Böhmer, D. Kraft and M. Tabatabai, Calixarenes 50th Anniversary, ed. by J. Vicens, Z. Asfari and J. M. Harrowfield, Kluwer Academic Press, Dordrecht, 1994, p. 17. In these references optical resolution of racemates has been accomplished.
17. P. A. Reddy and C. D. Gutsche, J. Org. Chem., 1993, 58, 3254;
18. W. Verboom, P. J. Bodewes, G. van Essen, P. Timmerman, G. J. van Hummel, S. Harkema and D. N. Reinhoudt, Tetrahedron, 1995, 51, 499. In these examples inherently chiral calix[4]arenes were synthesized but optical resolution was not attempted.
19. A few examples of naphthalene-based calix[4]arene derivatives have already appeared although the yields are generally very low: P. E. Georghiou and L. Zhaopeng, Calixarenes 50th Anniversary, ed. by J. Vicens, Z. Asfari and J. M. Harrowfield, Kluwer Academic Press, Dordrecht, 1994, p. 55;
20. G. D. Andreetti, V. Böhmer, J. G. Jordon, M. Tabatabai, F. Ugozzoli, W. Vogt and A. Wolff, J. Org. Chem., 1993, 58, 4023;
21. P. E. Georghiou, M. Ashram, Z. Li and S. G. Chaulk, J. Org. Chem., 1995, 60, 7284.
22. J. R. Zoeller and C. E. Summer, J. Org. Chem., 1990, 55, 319.
23. A. Ikeda and S. Shinkai, J. Chem. Soc., Perkin Trans. 1, 1993, 2671.
24. 14 Thus, we first used 1,2-dihydroxynaphthalene instead of 3-hydroxymethyl-2-naphthol. However, the desired staple reaction hardly proceeded while the decomposition of 8 (or its partially substituted products) gradually took place.
25. Y. Inoue, C. Fujimoto, K. Wada, A. Tai and T. Hakushi, J. Chem. Soc., Chem. Commun., 1987, 393;
26. T. Arimura, M. Kubota, T. Matsuda and S. Shinkai, Bull. Chem. Soc. Jpn., 1989, 62, 1674 and references cited therein.
27. In addition, we recently succeeded in immobilization of calix[6]arene by ring bridging and optical resolution of the enantiomers (the molecular asymmetry was induced by a substituent in the cap): H. Otsuka and S. Shinkai, J. Am. Chem. Soc., 1996, 118, 4274.
28. W. Verboon, S. Datta, Z. Asfari, S. Harkema and D. N. Reinhoudt, J. Org. Chem., 1992, 57, 5394.
29. T. Nagasaki, K. Sisido, T. Arimura and S. Shinkai, Tetrahedron, 1992, 48, 797.