Breaking the C3-symmetry of chiral tripodal oxazolines: Enantio-discrimination of chiral organoammonium ions

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7227-7231

  Kim, Jeongryul ^a   Kim, Sung Gon ^a   Seong, Hye Ran ^a   Ahn, Kyo Han ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC CHEMICALS; SYNTHESIS (CHEMICAL);

CHIRAL ORGANOAMMONIUM IONS; ENANTIODISCRIMINATION; ENANTIOSELECTIVE RECOGNITION BEHAVIOR; HOST-GUEST COMPLEX MODE;

AMMONIUM COMPOUNDS;

AMMONIUM DERIVATIVE; ION; ORGANOAMMONIUM ION; OXAZOLINE DERIVATIVE; PHENYLGLYCINE; RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; MOLECULAR RECOGNITION; RECEPTOR BINDING; STOICHIOMETRY; SYNTHESIS;

EID: 24144487692     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050872p     Document Type: Article

References (27)

1. (a) Bradshaw, J. S.; Izatt, R. M.; Bordunov, A. V.; Zhu, C. Y.; Hathaway, J. K. Crown Ethers. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon Press: New York, 1996; Vol. 1, PP 35-95.
2. (b) Gokel, G. W.; Abel, E. Complexation of Organic Cations. In Comprehensive Supramolecular Chemistry; Gokel, G. W., Ed.; Pergamon Press: New York, 1996; Vol. 1, pp 511-535.
3. 2 symmetric receptors, see: (a) Newcomb, M.; Toner, J. L.; Helgeson, R. C.; Cram, D. J. J. Am. Chem. Soc. 1979, 101, 4941-4947.
4. (b) Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393-406.
5. (c) Davidson, R. B.; Bradshaw, J. S.; Jones, B. A.; Dalley, N. K.; Christensen, J. J.; Izatt, R. M. J. Org. Chem. 1984, 49, 353-357.
6. (d) Iimori, T.; Erickson, S. D.; Rheingold, A. L.; Still, W. C. Tetrahedron Lett. 1989, 30, 6947-6950.
7. (e) Tsukuba, H.; Sohmiya, H. J. Org. Chem. 1991, 56, 875-878.
8. (f) Wang, X.; Erickson, S. D.; Iimori, T.; Still, W. C. J. Am. Chem. Soc. 1992, 114, 4128-4137.
9. (g) Miyake, H.; Yamashita, T.; Kojima, Y.; Tsukube, H. Tetrahedron Lett. 1995, 36, 7669-7672.
10. (h) You, J.-S.; Yu, X.-Q.; Zhang, G.-L.; Xing, Q.-X. Lan, J.-B.; Xie, R.-G. Chem. Commun. 2001, 1816-1817.
11. (a) Ahn, K. H.; Kim, S.-G.; Jung, J.; Kim, K-H.; Kim, J.; Chin, J.; Kim, K. Chem. Lett. 2000, 170-171.
12. (b) Kim, S.-G.; Ahn, K. H. Chem. Eur. J. 2000, 6, 3399-3403.
13. (c) Kim, S.-G.; Kim, K.-H.; Jung, J.; Shin, S. K.; Ahn, K. H. J. Am. Chem. Soc. 2002, 124, 591-596.
14. (d) Kim, S.-G.; Kim, K-H.; Kim, Y. K.; Shin, S. K.; Ahn, K. H. J. Am. Chem. Soc. 2003, 125, 13819-13824.
15. 3-symmetric receptors, see: (a) de Jong, F.; Siegel, M. G.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1975, 551-553.
16. (b) Löhr, H.-G.; Vögtle, F. Acc. Chem. Res. 1985, 18, 65-72.
17. (c) Hong, J.-I.; Namgoong, S. K.; Bernardi, A.; Still, W. C. J. Am. Chem. Soc. 1991, 113, 5111-5112.
18. (d) Pieters, R. J.; Diederich, F. Chem. Commun. 1996, 2255-2256.
19. 3-symmetric ligands used in asymmetric catalysis and chiral recognition, see: Moberg, C. Angew. Chem., Int. Ed. 1998, 37, 248-268.
20. Kim, S.-G.; Seong, H. R.; Kim, J.; Ahn, K. H. Tetrahedron Lett. 2004, 45, 6835-6838.
21. 2 is a harmful and dangerous chemical for human and the environment, and thus, it should be handled with proper caution.
22. See the Supporting Information.
23. Lein, G. M.; Cram, D. J. J. Am. Chem. Soc. 1985, 107, 448-455.
24. (a) Christensen, J. J.; Wrathall, D. P.; Oscarson, J. O.; Izatt, R. M. Anal. Chem. 1968, 40, 1713-1717.
25. (b) Smithrud, D. B.; Wyman, T. B.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420-5476.
26. (c) Rekharsky, M.; Inoue, Y. J. Am. Chem. Soc. 2000, 122, 4418-4435.
27. Molecular mechanics computation was performed using Spartan Windows '04 from Wavefunction, Inc. The computation used the MMFF94 force field and provided an isolated, equilibrium geometry at ground state. A geometry optimization could be readily done for the guest-bound region, for which region only a limited number of configurations resulted.