Enantiomeric discrimination by novel optically active isocyanurates having peripheral amino acid units

Tetrahedron Asymmetry

Volumn 11, Issue 10, 2000, Pages 2067-2075

  Sugimoto, Hiroshi ^a   Yamane, Yuuka ^a   Inoue, Shohei ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BINAPHTHOL; CYANURIC ACID; HYDROXYL GROUP; ISOCYANURIC ACID; METHOXYCARBONYLLEUCINE METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; MOLECULAR RECOGNITION; OPTICAL ROTATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; SYNTHESIS;

EID: 0034596010     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00165-8     Document Type: Article

References (20)

1. (a) Kaiser, E. T.; Kezdy, F. J. Science 1984, 223, 249.
2. (b) Morii, H.; Ichimura, K.; Uedaira, H. Proteins: Struct., Funct., Genet. 1991, 11, 133.
3. (c) Morii, H.; Hosoda, S.; Ohashi, S.; Uedaira, H. Biopolymers 1994, 34, 481.
4. (d) Nishino, N.; Sugita, Y.; Yamamoto, T.; Fujimoto, T. Rep. Asahi Glass Found. Ind. Technol. 1986, 48, 149.
5. (e) Sasaki, T.; Kaiser, E. T. J. Am. Chem. Soc. 1989, 111, 380.
6. (a) Cram, D. J.; Cram., J. M. Acc. Chem. Res. 1978, 11, 8.
7. (b) Lehn, J.-M. Pure Appl. Chem. 1978, 50, 871.
8. (c) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89.
9. (d) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009.
10. (a) Breslow, R.; Hammond, M.; Lauer, M. J. Am. Chem. Soc. 1980, 102, 421.
11. (b) Tabushi, I.; Kuroda, Y.; Yamada, M.; Higashimura, H. J. Am. Chem. Soc. 1985, 107, 5546.
12. For reviews of molecular recognition from the point of view of supramolecular chemistry, see: (a) Vögte, F. Supramolecular Chemistry; John Wiley & Sons: West Sussex, 1989. (b) Lehn, J.-M. Supramolecular Chemistry - Concepts and Perspectives; VCH: Weinheim, 1995.
13. For reviews of molecular recognition from the point of view of supramolecular chemistry, see: (a) Vögte, F. Supramolecular Chemistry; John Wiley & Sons: West Sussex, 1989. (b) Lehn, J.-M. Supramolecular Chemistry - Concepts and Perspectives; VCH: Weinheim, 1995.
14. 1H NMR measurement, however, the signals due to R-form and S-form were not separately observed at different chemical shifts.
15. c as resolving agent. (a) Pirkle, W. H.; Hoover, D. J. Top. Stereochem. 1982, 13, 263-264. (b) Rosini, C.; Uccello-Barretta, G.; Pini, D.; Abete, C.; Salvadori, P. J. Org. Chem. 1988, 53, 4579-4581. (c) Jursic, B. S.; Goldberg, S. I. J. Org. Chem. 1992, 57, 7172-7174.
16. c as resolving agent. (a) Pirkle, W. H.; Hoover, D. J. Top. Stereochem. 1982, 13, 263-264. (b) Rosini, C.; Uccello-Barretta, G.; Pini, D.; Abete, C.; Salvadori, P. J. Org. Chem. 1988, 53, 4579-4581. (c) Jursic, B. S.; Goldberg, S. I. J. Org. Chem. 1992, 57, 7172-7174.
17. c as resolving agent. (a) Pirkle, W. H.; Hoover, D. J. Top. Stereochem. 1982, 13, 263-264. (b) Rosini, C.; Uccello-Barretta, G.; Pini, D.; Abete, C.; Salvadori, P. J. Org. Chem. 1988, 53, 4579-4581. (c) Jursic, B. S.; Goldberg, S. I. J. Org. Chem. 1992, 57, 7172-7174.
18. Nowick, J. S.; Powell, N. A.; Nguyen, T. M.; Noronha, G. J. Org. Chem. 1992, 57, 7364.
19. Izumiya, N.; Kato, T.; Aoyagi, H.; Waki, M. Peputido Gousei no Kiso to Jikken, Maruzen 1986, 114-117.
20. Izumiya, N.; Kato, T.; Aoyagi, H.; Waki, M. Peputido Gousei no Kiso to Jikken, Maruzen 1986, 100-107.