Chiral recognition of amino acid derivatives by 1,1′-binaphthalene-8,8′-diol

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4153-4156

  Kawabata, Takeo ^a   Kuroda, Akio ^a,b   Nakata, Eizo ^a   Takasu, Kiyosei ^a   Fuji, Kaoru ^a  

^a KYOTO UNIVERSITY   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL DERIVATIVE; AMINO ACID DERIVATIVE; CADMIUM CHLORIDE; VALINE;

ARTICLE; CHIRALITY; COMPUTER MODEL; DIASTEREOISOMER; ENANTIOMER; HYDROGEN BOND; MOLECULAR RECOGNITION; MOLECULAR STABILITY;

EID: 0029981007     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00702-2     Document Type: Article

References (22)

1. W. H. Pirkle, T. C. Pochapsky, Chem. Rev., 89, 347 (1989).
2. W. H. Pirkle, E. M. Doherty, J. Am. Chem. Soc., 111, 4113 (1989).
3. E. N. Jacobsen, I. Marko, M. B. France, J. S. Svendsen, K. B. Sharpless, J. Am. Chem. Soc., 111, 737 (1989).
4. T. D. James, K. R. A. S. Sandanayaka, S. Shinkai, Nature, 374, 345 (1995).
5. a) J. -I. Hong, S. K. Namgoong, A. Bernardi, W. C. Still, J. Am. Chem. Soc., 113, 5111 (1991).
6. b) A. Galán, D. Andreu, A. M. Echavarren, P. Prados, J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
7. S. S. Flack, J. D. Kilburn, Tetrahedron Lett., 36, 3409 (1995).
8. X. Wang, S. D. Erickson, T. Iimori, W. C. Still, J. Am. Chem. Soc., 114, 4128 (1992).
9. a) P. P. Castro, T. M. Georgiadis, F. Diederich, J. Org. Chem., 54, 5835 (1989).
10. b) F. Garcia-Tellado, J. Albert, A. D. Hamilton., J. C. S. Chem. Comm., 1761 (1991).
11. K. Fuji, T. Kawabata, A. Kuroda, J. Org. Chem., 60, 1914 (1995).
12. Recently, another method for resolution of 1,1′-binaphthalene-8,8′-diol has been reported; D. Fabbri, G. Delogu, O. De Lucchi, J. Org. Chem., 60, 6599 (1995).
13. No significant binding between 3 and amino compounds was observed.
14. 0 are the initial host-and guest-concentration, respectively.* Analysis of data was performed by a commercial software, Excel (Microsoft). *M. Fujita, S. Nagao, M. Iida, K. Ogura, J. Am. Chem. Soc., 115, 1574 (1993).
15. 1H-NMR study could not be performed due to the poor solubility of the amino acids.
16. G. Chang, W.C. Still, J. Am. Chem. Soc., 111, 4379 (1989).
17. Monte-Carlo conformational search and AMBER* calculation was carried out by MacroModel V. 4.5. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comp. Chem., 11, 440 (1990).
18. The calculated distance between the carbxylate-oxygens and the phenolic hydrogens is 1.59-1.65 Å.
19. The calculated distance between the ammonium hydrogens and the nearest aromatic carbons is 2.38-2.46 Å. For a recent paper describing ammonium-π interaction, see; K. S. Kim, J. Y. Lee, S. J. Lee, T-K. Ha, D. H. Kim, J. Am. Chem. Soc., 116, 7399 (1994).
20. 2 and the nearest aromatic carbons is 3.05-3.09 Å. For an excellent review on CH-π interaction, see: M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron, 51, 8665 (1995).
21. The major difference between the calculated structures of the complexes of 4 and 1 and that of 4 and 2 is the location of the iso-propyl group of 4: The iso-propyl group points away from the naphthalene ring in the latter complex.
22. J. J. Gordon, J.P. Devlin, A. J. East, W. D. Ollis, I. O. Sutherland, D. E. Wright, L. Niet, J. C. S. Perkin I, 819 (1975).