A new class of chiral calix[4]arenes as receptors with planar chirality

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9013-9016

  Okada, Yukihiro ^a   Mizutani, Manabu ^a   Ishii, Fuyuhiko ^a   Nishimura, Jun ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; RECEPTOR;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; RACEMIC MIXTURE;

EID: 0030867171     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10408-7     Document Type: Article

References (19)

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3. Sousa, L. R.; Hoffman, D. H.; Kaplan, L.; Cram, D. J. J. Am. Chem. Soc. 1974, 96, 7100.
4. Harada, N.; Soutome, T.; Nehira, T; Uda, H.; Ui, S.; Okamura, A.; Miyano, S. J. Am. Chem. Soc. 1993, 115, 7547.
5. Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon, Y. Angew. Chem. Int. Ed. Engl. 1994, 33, 91.
6. Calixarenes 50th Anniversary; Vicens, J.; Asfari, Z.; Harrowfield, J. M., Eds.; Kluwer: Dordrecht, 1994.
7. Shinkai, S.; Arimura, T.; Kawabata, H.; Murakami, H.; Araki, K.; Iwamoto, K.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1990, 1734; Okada, Y.; Kasai, Y.; Nishimura, J. Tetrahedron Lett. 1995, 36, 555.
8. Shinkai, S.; Arimura, T.; Kawabata, H.; Murakami, H.; Araki, K.; Iwamoto, K.; Matsuda, T. J. Chem. Soc., Chem. Commun. 1990, 1734; Okada, Y.; Kasai, Y.; Nishimura, J. Tetrahedron Lett. 1995, 36, 555.
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11. (c) Okada, Y.; Ishii, F.; Kasai, Y.; Nishimura, J. Tetrahedron Lett. 1993, 34, 1971;
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15. (g) Okada, Y.; Ishii, F.; Kasai, Y.; Nishimura, J. Tetrahedron 1994, 50, 12159;
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19. 3, δ (intensity, multiplicity, J in Hz); 2a, -0.32 (1H, m), -0.19 (1H, m), 0.58 (2H, m), 1.31 (4H, m), 1.68 (4H, m), 2.13 (1H, m), 2.20 - 2.60 (10H, m), 2.61 - 2.84 (5H, m), 3.14 (1H, d, 14), 3.22 (1H, d, 14), 3.64 (1H, d, 14), 3.81 (1H, d, 14), 3.82 (3H, s), 4.25 (1H, m), 4.40 (1H, m), 4.56 (1H, q-like), 4.58 (1H, m), 5.51 (1H, s), 6.59 (1H, d, 2.0), 6.66 (1H, d, 2.0), 6.67 (1H, d, 2.0), 6.70 (1H, d, 2.0), 6.94 (2H, d, 2.0), 6.98 (1H, d, 2.0), 7.15 (1H, d, 2.0), 7.16 (1H, s), 7.91 (1H, s); 2b, -0.32 (1H, m), -0.17 (1H, m), 0.57 (2H, m), 1.30 (6H, m), 1.56 (3H, t, 7.0), 1.60 - 1.84 (4H, m), 2.09 (1H, m), 2.22 - 2.59 (8H, m), 2.70 (4H, m), 2.80 (1H, m), 3.14 (1H, d, 14), 3.21 (1H, d, 14), 3.64 (1H, d, 14), 3.82 (1H, d, 14), 3.88 (2H, q, 7.0), 4.26 (1H, m), 4.36 (1H, m), 4.55 (1H, q-like), 4.60 (1H, m), 5.61 (1H, s), 6.59 (1H, d, 1.8), 6.66 (1H, d, 1.8), 6.68 (1H, d, 1.8), 6.69 (1H, d, 1.8), 6.94 (2H, d, 1.8), 6.98 (1H, d, 1.8), 7.15 (1H, d, 1.8), 7.22 (1H, s), 7.95 (1H, s); 3a, -0.20 (2H, m), 0.57 (2H, m), 1.26 (2H, m), 1.38 (2H, m), 1.72 (4H, m), 2.04 (2H, m), 2.32 (4H, m), 2.40 (2H, m), 2.69 (6H, m), 2.76 (2H, m), 3.21 (2H, d, 13), 3.69 (2H, d, 13), 3.78 (6H, s), 4.38 (2H, m), 4.61 (2H, q-like), 6.62 (2H, d, 2.1), 6.67 (2H, d, 2.1), 6.98 (2H, d, 2.1), 7.14 (2H, d, 2.1), 7.79 (2H, s); 3b, -0.18 (2H, m), 0.53 (2H, m), 1.25 (2H, m), 1.38 (2H, m), 1.55 (6H, t, 7.0), 1.72 (4H, m), 1.98 (2H, m), 2.30 (4H, m), 2.40 (2H, m), 2.68 (6H, m), 2.81 (2H, m), 3.20 (2H, d, 13), 3.70 (2H, d, 13), 3.83 (2H, q, 7.0), 3.86 (2H, q, 7.0), 4.36 (2H, m), 4.60 (2H, q-like), 6.63 (2H, d, 1.8), 6.66 (2H, d, 1.8), 6.98 (2H, d, 1.8), 7.14 (2H, d, 1.8), 7.73 (2H, s); 5a, -0.14 (2H, m), 0.64 (2H, m), 1.24 (2H, m), 1.43 (2H, m), 1.78 (4H, m), 2.10 - 2.83 (16H, m), 3.00 (1H, d, 14), 3.21 (1H, d, 14), 3.42 (3H, s), 3.63 (1H, d, 14), 3.66 (3H, s), 3.74 (3H, s), 4.39 (1H, d, 14), 4.39 (1H, m), 4.44 (1H, m), 4.54 (1H, q-like), 4.58 (1H, q-like), 6.65 (1H, d, 1.8), 6.73 (1H, s), 6.73 (1H, d, 1.8), 6.81 (1H, d, 1.8), 6.91 (1H, d, 1.8), 7.01 (1H, d, 1.8), 7.06 (1H, d, 1.8), 7.11 (1H, d, 1.8), 7.19 (1H, d, 1.8); 5b, -0.15 (2H, m), 0.61 (2H, m), 1.26 (2H, m), 1.46 (2H, m), 1.52 (3H, t, 7.0), 1.53 (6H, m), 1.63 - 1.89 (4H, m), 2.05 (1H, m), 2.23 (1H, m), 2.27 - 2.58 (6H, m), 2.60 - 2.80 (8H, m), 3.00 (1H, d, 13), 3.13 (1H, m), 3.22 (1H, d, 14), 3.39 (1H, m), 3.62 (1H, d, 14), 3.67 (2H, q, 7.0), 3.82 (2H, m), 4.26 (1H, m), 4.43 (1H, d, 13), 4.43 (1H, m), 4.56 (2H, m), 6.65 (1H, d, 1.8), 6.74 (1H, s), 6.75 (1H,d, 1.8), 6.85 (1H, d, 1.8), 6.93 (1H, d, 1.8), 7.00 (1H, d, 1.8), 7.07 (1H, d, 1.8), 7.14 (1H, d, 1.8), 7.20 (1H, d, 1.8); 7a, -0.07 (2H, m), 0.72 (2H, m), 1.32 (2H, m), 1.43 (2H, m), 1.56 (2H, m), 1.78 (4H, m), 2.27 - 2.53 (8H, m), 2.59 (4H, m), 2.63 - 2.80 (4H, m), 2.99 (2H, d, 14), 3.67 (6H, s), 3.72 (2H, m), 3.80 - 3.96 (10H, m), 4.12 (2H, m), 4.28 (2H, d, 14), 4.50 (4H, m), 6.91 (2H, d, 2.0), 6.94 (2H, d, 2.0), 7.03 (2H, d, 2.0), 7.09 (2H, d, 2.0); 7b, 0.00 (2H, m), 0.77 (2H, m), 1.41 (2H, m), 1.51 (6H, t, 7.0), 1.79 (4H, m), 2.30 (2H, m), 2.39 (2H, m), 2.49 (8H, m), 2.64 - 2.80 (4H, m), 2.98 (2H, d, 13), 3.56 - 3.80 (10H, m), 3.85 (4H, q, 7.0), 3.92 (2H, m), 4.06 - 4.22 (4H, m), 4.31 (2H, d, 13), 4.46 (4H, m), 6.89 (2H, d, 2.0), 6.95 (2H, d, 2.0), 7.03 (2H, d, 2.0), 7.08 (2H, d, 2.0).