Synthesis of chiral calix[4]resorcinarenes via Mono-O-benzylation. Complexation behavior with a chiral trimethylammonium compound

Chemistry Letters

Volumn , Issue 8, 1996, Pages 685-686

  Konishi, Hisatoshi ^a   Tamura, Takashi ^a   Ohkubo, Hiromichi ^a   Kobayashi, Kazuhiro ^a   Morikawa, Osamu ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030521348     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.685     Document Type: Article

References (17)

1. C. D. Gutsche, "Calixarenes," The Royal Society of Chemistry, Cambridge (1989).
2. T. Fujimoto, R. Yanagihara, K. Kobayashi, and Y. Aoyama, Bull. Chem. Soc. Jpn., 68, 2113 (1995), and references therein.
3. M. Inouye, K. Hashimoto, and K. Isagawa, J. Am. Chem. Soc., 116, 5517 (1994).
4. D.J. Cram and J.M. Cram, "Container Molecules and Their Guests," The Royal Society of Chemistry, Cambridge (1994).
5. Calix[4]resorcinarenes possessing chiral amine substituents at 2-position of resorcinol nuclei have been synthesized: (a) Y. Matsushita and T. Matsui, Tetrahedron Lett., 46, 7433 (1993),
6. (b) R. Yanagihara, M. Tominaga, and Y. Aoyama, J. Org. Chem., 59, 6865 (1994),
7. (c) U. Schneider and H.-J. Schneider, Chem. Ber., 127, 2455 (1994).
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9. A. G. S. Högberg, J. Am. Chem. Soc., 102, 6046 (1980).
10. The synthesis of chiral calixarenes and their analogs by partial and regioselective O-alkylation has been studied: (a) K. Araki, K. Inada, and S. Shinkai, Angew. Chem. Int. Ed. Engl. 35, 72 (1996),
11. (b) K. Iwamoto, H. Shimizu, K. Araki, and S. Shinkai, J. Am. Chem. Soc., 115, 3997 (1993),
12. (c) G. Ferguson, J. F. Gallagher, L. Giunta, P. Neri, S. Pappalardo, and M. Parisi, J. Org. Chem., 59, 42 (1994),
13. (d) Y. Okada, F. Ishii, Y. Kasai, and J. Nishimura, Chem. Lett., 755 (1992).
14. The conformer distribution was determined by the integration of the signals of benzyl methylene protons, which appeared as two AB quartets (4.557, 4.693, J=11Hz, the major isomer) and (5.046, 5.104, J=10Hz, the miner isomer).
15. 3 at -30°C, the aromatic protons of the macrocycle resonate at δ 5.925, 5.935, 6.407, 6.747, 6.893, 6.937, 7.236, 7.410 ppm.
16. H.-J. Schneider, D. Güttes, and U. Schneider, J. Am. Chem. Soc., 110, 6449 (1988).
17. K. Kobayashi, Y. Asakawa, and Y. Aoyama, Supramolecular Chem., 2, 133 (1993).